Chemical compounds

ABSTRACT

Provided herein are novel and useful compounds having a tryptase inhibition activity, pharmaceutical compositions comprising such compounds, and methods treating subjects suffering from a condition, disease, or disorder that can be ameliorated by the administration of an inhibitor of tryptase, e.g., asthma and inflammatory diseases, to name only a few.

FOREIGN PRIORITY CLAIM

This application claims priority under 35 U.S.C. § 119 of United Kingdompatent application number 0012362.0 filed May 22, 2000, which is herebyincorporated by reference herein in its entirety.

FIELD OF THE INVENTION

This invention is directed to substituted arylmethylamines, theirpreparation, pharmaceutical compositions containing these compounds, andtheir pharmaceutical use in the treatment of disease states capable ofbeing modulated by the inhibition of tryptase.

BACKGROUND OF THE INVENTION

Tryptase is stored in mast cell secretory granules and is the majorsecretory protease of human mast cells. Tryptase has been implicated ina variety of biological processes, including degradation of vasodilatingand bronchorelaxing neuropeptides (Caughey, et al., J. Pharmacol. Exp.Ther., 1988, 244, pages 133-137; Franconi, et al., J. Pharmacol. Exp.Ther., 1988, 248, pages 947-951; and Tam, et al., Am. J. Respir. CellMol. Biol., 1990, 3, pages 27-32) and modulation of bronchialresponsiveness to histamine (Sekizawa, et al., J. Clin. Invest., 1989,83, pages 175-179). As a result, tryptase inhibitors may be useful asanti-inflammatory agents (K Rice, P. A. Sprengler, Current Opinion inDrug Discovery and Development, 1999, 2(5), pages 463-474) particularlyin the treatment of chronic asthma (M. Q. Zhang, H. Timmerman, MediatorsInflamm., 1997, 112, pages 311-317) and may also be useful in treatingor preventing allergic rhinitis (S. J. Wilson et al, Clin. Exp. Allergy,1998, 28, pages 220-227), inflammatory bowel disease (S. C. Bischoff etal, Histopathology, 1996, 28, pages 1-13), psoriasis (A. Naukkarinen etal, Arch. Dermatol. Res., 1993, 285, pages 341-346), conjunctivitis (A.A. Irani et al, J. Allergy Clin. Immunol., 1990, 86, pages 34-40),atopic dermatitis (A. Jarvikallio et al, Br. J. Dermatol., 1997, 136,pages 871-877), rheumatoid arthritis (L. C Tetlow et al, Ann. Rheum.Dis., 1998, 54, pages 549-555), osteoarthritis (M. G. Buckley et al, J.Pathol., 1998, 186, pages 67-74), gouty arthritis, rheumatoidspondylitis, and diseases of joint cartilage destruction.

In addition, tryptase has been shown to be a potent mitogen forfibroblasts, suggesting its involvement in the pulmonary fibrosis inasthma and interstitial lung diseases (Ruoss et al., J. Clin. Invest.,1991, 88, pages 493-499). Therefore, tryptase inhibitors may be usefulin treating or preventing fibrotic conditions (J. A. Cairns and A. F.Walls, J. Clin. Invest., 1997, 99, pages 1313-1321) for example,fibrosis, sceleroderma, pulmonary fibrosis, liver cirrhosis, myocardialfibrosis, neurofibromas and hypertrophic scars.

Additionally, tryptase inhibitors may be useful in treating orpreventing myocardial infarction, stroke, angina and other consequencesof atherosclerotic plaque rupture (M. Jeziorska et al, J. Pathol., 1997,182, pages 115-122). Tryptase has also been discovered to activateprostromelysin that in turn activates collagenase, thereby initiatingthe destruction of cartilage and periodontal connective tissue,respectively. Therefore, tryptase inhibitors could be useful in thetreatment or prevention of arthritis, periodontal disease, diabeticretinopathy, and tumor growth (W. J. Beil et al, Exp. Hematol., (1998)26, pages 158-169). Also, tryptase inhibitors may be useful in thetreatment of anaphylaxis (L. B. Schwarz et al, J. Clin. Invest., 1995,96, pages 2702-2710), multiple sclerosis (M. Steinhoff et al, Nat. Med.(N. Y.), 2000, 6(2), pages 151-158), peptic ulcers and syncytial viralinfections.

Mast cell mediated inflammatory conditions, in particular asthma, are agrowing public health concern. Asthma is frequently characterized byprogressive development of hyper-responsiveness of the trachea andbronchi to both immunospecific allergens and generalized chemical orphysical stimuli, which lead to the onset of chronic inflammation.Leukocytes containing IgE receptors, notably mast cells and basophils,are present in the epithelium and underlying smooth muscle tissues ofbronchi. These leukocytes initially become activated by binding ofspecific inhaled antigens to the IgE receptors and then release a numberof chemical mediators. For example, degranulation of mast cells leads tothe release of proteoglycans, peroxidase, arylsulfatase B, tryptase andchymase, which results in bronchiole constriction.

Accordingly, what is needed is a novel and useful group of compoundshaving valuable pharmaceutical properties, particularly, the ability toinhibit tryptase. Such compounds readily have utility in treating apatient suffering condition that can be ameliorated by theadministration of an inhibitor of tryptase, e.g., mast cell mediatedinflammatory conditions, inflammation, and diseases or disorders relatedto the degradation of vasodilating and bronchorelaxing neuropeptides.Particular examples of such conditions are described infra.

The citation of any reference herein should not be construed as anadmission that such reference is available as “Prior Art” to the instantapplication.

SUMMARY OF THE INVENTION

Broadly, the present invention extends to a compound of formula (I):

such that Ar is an aryl group or a heteroaryl group, and the

group is beta to the

group on the aryl,wherein:

is a single or a double bond;

-   -   R¹ and R² are each independently hydrogen or lower alkyl;    -   R³ is aryl, arylalkenyl, cycloalkenyl, cycloalkyl, heteroaryl,        heteroarylalkenyl, heterocycloalkenyl, a carbon linked        heterocycloalkyl or alkyl optionally substituted by one or more        groups selected from hydroxy, alkoxy, alkyloxycarbonylamino,        cycloalkyl, heterocycloalkyl, R⁶, —OR⁶, —S(O)_(m)R⁶ or        —C(═O)—R⁶;    -   R⁴ is hydrogen, acyl, alkoxy, alkyloxycarbonyl, carboxy, cyano,        halo, hydroxy, —C(═O)—NY¹Y² or alkyl optionally substituted with        alkoxy, alkylcarbonylamino, alkylsulfonylamino, hydroxy,        —S(O)_(m)-alkyl or —NY¹Y²;    -   R⁵ is hydrogen, acyl, alkoxy, alkyloxycarbonyl, aryl, carboxy,        cyano, halo, heteroaryl, heteroaryloxy, heterocycloalkyl,        heterocycloalkyloxy, heterocycloalkylalkyloxy,        heteroarylalkyloxy, hydroxy, trifluoromethyl, —C(═O)—NY¹Y²,        —NY¹Y², —Z¹—C₂₋₆alkylene-R⁷ or alkyl optionally substituted with        alkoxy, alkylcarbonylamino, alkylsulfonylamino, aryl,        heteroaryl, heterocycloalkyl, hydroxy, ureido, —C(═O)—NY¹Y²,        —SO₂—NY¹Y², —S(O)_(m)-alkyl or —NY¹Y²;    -   R⁶ is aryl or heteroaryl;    -   R⁷ is hydroxy, alkoxy, ureido, —C(═O)—NY¹Y², —SO₂—NY¹Y²,        —S(O)_(m)-alkyl or —NY¹Y²;    -   R⁸ is hydrogen or lower alkyl;    -   Y¹ and Y² are independently hydrogen, alkenyl, alkyl, aryl,        arylalkyl, cycloalkyl, heteroaryl, heteroarylalkyl or        heterocycloalkyl; or the group —NY¹Y² may form a cyclic amine;    -   Z¹ is O, S(O)_(m) or NR⁸;    -   m is zero or an integer 1 to 2;    -   n is zero or an integer 1 to 4;        an N-oxide of said compound, a prodrug of said compound, a        pharmaceutically acceptable salt of said compound, a solvate of        said compound, and a hydrate of said compound.

Furthermore, the present invention extends to a compound of formula(Ia):

wherein:

is a single or a double bond;

-   -   R¹ and R² are each independently hydrogen or lower alkyl;    -   R³ is aryl, arylalkenyl, cycloalkenyl, cycloalkyl, heteroaryl,        heteroarylalkenyl, heterocycloalkenyl, a carbon linked        heterocycloalkyl or alkyl optionally substituted by one or more        groups selected from hydroxy, alkoxy, alkyloxycarbonylamino,        cycloalkyl, heterocycloalkyl, R⁶, —OR⁶, —S(O)_(m)R⁶ or        —C(═O)—R⁶;    -   R⁴ is hydrogen, acyl, alkoxy, alkyloxycarbonyl, carboxy, cyano,        halo, hydroxy, —C(═O)—NY¹Y² or alkyl optionally substituted with        alkoxy, alkylcarbonylamino, alkylsulfonylamino, hydroxy,        —S(O)_(m)-alkyl or —NY¹Y²;    -   R⁵ is hydrogen, acyl, alkoxy, alkyloxycarbonyl, aryl, carboxy,        cyano, halo, heteroaryl, heteroaryloxy, heterocycloalkyl,        heterocycloalkyloxy, heterocycloalkylalkyloxy,        heteroarylalkyloxy, hydroxy, trifluoromethyl, —C(═O)—NY¹Y²,        —NY¹Y², —Z¹—C₂₋₆alkylene-R⁷ or alkyl optionally substituted with        alkoxy, alkylcarbonylamino, alkylsulfonylamino, aryl,        heteroaryl, heterocycloalkyl, hydroxy, ureido, —C(═O)—NY¹Y²,        —SO₂—NY¹Y², —S(O)_(m)-alkyl or —NY¹Y²;    -   R⁶ is aryl or heteroaryl;    -   R⁷ is hydroxy, alkoxy, ureido, —C(═O)—NY¹Y², —SO₂—NY¹Y²,        —S(O)_(m)-alkyl or —NY¹Y²;    -   R⁸ is hydrogen or lower alkyl;    -   Y¹ and Y² are independently hydrogen, alkenyl, alkyl, aryl,        arylalkyl, cycloalkyl, heteroaryl, heteroarylalkyl or        heterocycloalkyl; or the group —NY¹Y² may form a cyclic amine;    -   Z¹ is O, S(O)_(m) or NR⁸;    -   m is zero or an integer 1 to 2;    -   n is zero or an integer 1 to 4;        and the corresponding N-oxides, and their prodrugs; and        pharmaceutically acceptable salts and solvates (e.g. hydrates)        of such compounds and their N-oxides and prodrugs.

2. In another embodiment, the present invention extends to a compound offormula (Ib):

wherein

-   -   R³ is aryl, arylalkenyl, cycloalkenyl, cycloalkyl, heteroaryl,        heteroarylalkenyl, heterocycloalkenyl, a carbon linked        heterocycloalkyl or alkyl optionally substituted by one or more        groups selected from hydroxy, alkoxy, alkyloxycarbonylamino,        cycloalkyl, heterocycloalkyl, R⁶, —OR⁶, —S(O)_(m)R⁶ or        —C(═O)—R⁶;    -   R⁴ is hydrogen, acyl, alkoxy, alkyloxycarbonyl, carboxy, cyano,        halo, hydroxy, —C(═O)—NY¹Y² or alkyl optionally substituted with        alkoxy, alkylcarbonylamino, alkylsulfonylamino, hydroxy,        —S(O)_(m)-alkyl or —NY¹Y²; and    -   R⁵ is hydrogen, acyl, alkoxy, alkyloxycarbonyl, aryl, carboxy,        cyano, halo, heteroaryl, heteroaryloxy, heterocycloalkyl,        heterocycloalkyloxy, heterocycloalkylalkyloxy,        heteroarylalkyloxy, hydroxy, trifluoromethyl, —C(═O)—NY¹Y²,        —NY¹Y², —Z¹-C₂₋₆alkylene-R⁷ or alkyl optionally substituted with        alkoxy, alkylcarbonylamino, alkylsulfonylamino, aryl,        heteroaryl, heterocycloalkyl, hydroxy, ureido, —C(═O)—NY¹Y²,        —SO₂—N¹Y², —S(O)_(m)-alkyl or —NY¹Y², and,    -   a corresponding N-oxide of said compound, a prodrug of said        compound, a pharmaceutically acceptable salt of said compound, a        solvate of said compound, an N-oxides and prodrugs.

Particular examples of such compounds are described infra.

Furthermore, the present invention extends to a pharmaceuticalcomposition comprising a compound of the present invention, as describedabove, and a pharmaceutically acceptable carrier thereof. Numerousexamples of pharmaceutical carriers having applications in the presentinvention are described infra.

In addition, the present invention extends to a method for treating apatient suffering from a condition that can be ameliorated by theadministration of an inhibitor of tryptase, comprising administering aneffective amount of a compound of a compound of the present invention.An example of a condition that can be treated with a compound of thepresent invention includes, but certainly is not limited to inflammatorydiseases, e.g., joint inflammation, arthritis, rheumatoid arthritis,rheumatoid spondylitis, gouty arthritis, traumatic arthritis, rubellaarthritis, psoriatic arthritis, and other chronic inflammatory jointdiseases. Other examples of conditions that can be treated with a methodof the present invention include diseases of joint cartilagedestruction, ocular conjunctivitis, vernal conjunctivitis, inflammatorybowel disease, asthma, allergic rhinitis, interstitial lung diseases,fibrosis, sceleroderma, pulmonary fibrosis, liver cirrhosis, myocardialfibrosis, neurofibromas, hypertrophic scars, various dermatologicalconditions, for example, atopic dermatitis and psoriasis, myocardialinfarction, stroke, angina and other consequences of atheroscleroticplaque rupture, as well as periodontal disease, diabetic retinopathy,tumor growth, anaphylaxis, multiple sclerosis, peptic ulcers, andsyncytial viral infections, to name only a few.

In a particular embodiment, the present invention extends to a method oftreating a subject suffering from asthma, comprising administering tothe subject an effective amount of a compound of the present invention.

In another embodiment, the present invention extends to a method fortreating a patient suffering from joint inflammation, comprisingadministering to the patient an effective amount of a compound of thepresent invention.

In addition, the present invention extends to a pharmaceuticalcomprising a compound of the present invention, a second compoundselected from the group consisting of a beta andrenergic agonist, ananticholinergic, an anti-inflammatory corticosteroid, and ananti-inflammatory agent, and a pharmaceutically acceptable carrierthereof. Particular inflammatory diseases or disorders that can betreated with such a pharmaceutical composition includes, but certainlyis not limited to asthma.

Moreover, the present invention extends to a method for treating apatient suffering from an inflammatory disorder, comprisingadministering to the patient a compound of the present invention and asecond compound selected from the group consisting of a beta andrenergicagonist, an anticholinergic, an anti-inflammatory corticosteroid, and ananti-inflammatory agent. In such a method of the present invention, acompound of the present invention can be administered to the patientbefore a second compound, a second compound can be administered to thepatient before a compound of the present invention, or a compound of thepresent invention and a second compound can be administeredconcurrently. Particular examples of andrenergic agonists,anticholinergics, anti-inflammatory corticosteroids, andanti-inflammatory agents having applications in a method of the presentinvention are described infra.

Accordingly, it is a principal object to provide compounds having ananti-tryptase activity. Such compounds can readily be used to treat acondition that can be ameliorated by the administration of an inhibitorof tryptase.

It is another object of the present invention to provide pharmaceuticalcompositions for treating a condition that can be ameliorated by theadministration of an inhibitor of tryptase.

It is yet another object of the present invention to providepharmaceutical compositions comprising a compound of the presentinvention.

These and other aspects of the present invention will be betterappreciated by reference to the following Detailed Description.

DETAILED DESCRIPTION

As used above, and throughout the instant specification and appendingclaims, the following terms, unless otherwise indicated, shall beunderstood to have the following meanings:

As used herein, the term “compounds of the present invention”, andequivalent expressions, are meant to embrace compounds of formulae (I),(Ia), or (Ib) as hereinbefore described, which expression includes theprodrugs, the pharmaceutically acceptable salts and the solvates, e.g.hydrates, where the context so permits. Similarly, reference tointermediates, whether or not they themselves are claimed, is meant toembrace their salts, and solvates, where the context so permits. For thesake of clarity, particular instances when the context so permits aresometimes indicated in the text, but these instances are purelyillustrative and it is not intended to exclude other instances when thecontext so permits.

As used herein, the term “treatment” includes prophylactic therapy aswell as treatment of an established condition.

“Patient” includes both human and other mammals.

“Effective amount” is meant to describe an amount of compound of thepresent invention effective in inhibiting tryptase and thus producingthe desired therapeutic effect.

“Acyl” means an H—CO— or alkyl-CO— group in which the alkyl group is asdescribed herein.

“Acylamino” is an acyl-NH— group wherein acyl is as defined herein.

“Alkenyl” means an aliphatic hydrocarbon group containing acarbon-carbon double bond and which may be straight or branched havingabout 2 to about 15 carbon atoms in the chain. Preferred alkenyl groupshave 2 to about 12 carbon atoms in the chain; and more preferably about2 to about 4 carbon atoms in the chain. “Branched”, as used herein andthroughout the text, means that one or more lower alkyl groups such asmethyl, ethyl or propyl are attached to a linear chain; here a linearalkenyl chain. “Lower alkenyl” means about 2 to about 4 carbon atoms inthe chain that may be straight or branched. Exemplary alkenyl groupsinclude ethenyl, propenyl, n-butenyl, i-butenyl, 3-methylbut-2-enyl,n-pentenyl, heptenyl, octenyl and decenyl.

“Alkoxy” means an alkyl-O— group in which the alkyl group is asdescribed herein. Exemplary alkoxy groups include methoxy, ethoxy,n-propoxy, i-propoxy, n-butoxy and heptoxy.

“Alkyloxycarbonyl” means an alkyl-O—C(═O)— group in which the alkylgroup is as described herein. Exemplary alkyloxycarbonyl groups includemethoxy- and ethoxycarbonyl.

“Alkyl” means, unless otherwise specified, an aliphatic hydrocarbongroup which may be straight or branched having about 1 to about 15carbon atoms in the chain optionally substituted by alkoxy or by one ormore halogen atoms. Particular alkyl groups have from 1 to about 6carbon atoms. “Lower alkyl” as a group or part of a lower alkoxy, loweralkylthio, lower alkylsulfinyl or lower alkylsulfonyl group means unlessotherwise specified, an aliphatic hydrocarbon group which may bestraight or branched having about 1 to about 4 carbon atoms in thechain. Exemplary alkyl groups include methyl, ethyl, n-propyl, i-propyl,n-butyl, s-butyl, t-butyl, n-pentyl, 3-pentyl, heptyl, octyl, nonyl,decyl and dodecyl.

“Alkylcarbonylamino” means an alkyl-C(═O)—NH— group in which the alkylgroup is as described herein. Exemplary alkylcarbonylamino groupsinclude acetamido and propionamido.

“Alkylene” means an aliphatic bivalent radical derived from a straightor branched alkyl group, in which the alkyl group is as describedherein. Exemplary alkylene radicals include methylene, ethylene andtrimethylene.

“Alkylenedioxy” means an -O-alkyl-O— group in which the alkyl group isas defined above. Exemplary alkylenedioxy groups include methylenedioxyand ethylenedioxy.

“Alkylsulfinyl” means an alkyl-SO— group in which the alkyl group is aspreviously described. Preferred alkylsulfinyl groups are those in whichthe alkyl group is C₁₋₄alkyl.

“Alkylsulfonyl” means an alkyl-SO₂- group in which the alkyl group is aspreviously described. Preferred alkylsulfonyl groups are those in whichthe alkyl group is C₁₋₄alkyl.

“Alkylsulfonylamino” means an alkyl-SO₂—NH— group in which the alkylgroup is as described herein. Exemplary alkylsulfonylamino groupsinclude methanesulfonamido and ethanesulfonamido.

“Alkylthio” means an alkyl-S— group in which the alkyl group is aspreviously described. Exemplary alkylthio groups include methylthio,ethylthio, isopropylthio and heptylthio.

“Alkynyl” means an aliphatic hydrocarbon group containing acarbon-carbon triple bond and which may be straight or branched havingabout 2 to about 15 carbon atoms in the chain. Preferred alkynyl groupshave 2 to about 12 carbon atoms in the chain; and more preferably about2 to about 4 carbon atoms in the chain. Exemplary alkynyl groups includeethynyl, propynyl, n-butynyl, 2-butynyl, 3-methylbut-2-ynyl, andn-pentynyl.

“Aroyl” means an aryl-CO— group in which the aryl group is as describedherein. Exemplary aroyl groups include benzoyl and 1- and 2-naphthoyl.

“Aroylamino” is an aroyl-NH— group wherein aroyl is as previouslydefined.

“Aryl” as a group or part of a group denotes: (i) an optionallysubstituted monocyclic or multicyclic aromatic carbocyclic moiety ofabout 6 to about 14 carbon atoms, such as phenyl or naphthyl; or (ii) anoptionally substituted partially saturated multicyclic aromaticcarbocyclic moiety in which an aryl and a cycloalkyl or cycloalkenylgroup are fused together to form a cyclic structure, such as atetrahydronaphthyl, indenyl or indanyl ring. Aryl groups may besubstituted with one or more aryl group substituents which may be thesame or different, where “aryl group substituent” includes, for example,acyl, acylamino, alkoxy, alkyloxycarbonyl, alkylenedioxy, alkylsulfinyl,alkylsulfonyl, alkylthio, aroyl, aroylamino, aryl, arylalkenyl,arylalkynyl, arylalkyloxy, arylalkyloxycarbonyl, arylalkylthio, aryloxy,aryloxyalkyl, aryloxycarbonyl, arylsulfinyl, arylsulfonyl, arylthio,carboxy, cyano, halo, heteroaroyl, heteroaryl, heteroarylalkenyl,heteroarylalkynyl, heteroarylalkyloxy, heteroaroylamino, heteroaryloxy,heteroaryloxyalkyl, hydroxy, nitro, trifluoromethyl, —NY¹Y², —CONY¹Y²,—SO₂NY¹Y², —Z²—C₂₋₆alkylene-NY¹Y² {where Z² is O, NR⁸ or S(O)_(m)},—NY¹—(C═O)alkyl, —NY¹—SO₂alkyl or alkyl optionally substituted withalkoxy, aroyl, aryl, aryloxy, heteroaryl, hydroxy, or —NY¹Y².

“Arylalkenyl” means an aryl-alkenyl- group in which the aryl and alkenylare as previously described. Preferred arylalkenyls contain a loweralkenyl moiety. Exemplary arylalkenyl groups include styryl andphenylallyl.

“Arylalkyl” means an aryl-alkyl- group in which the aryl and alkylmoieties are as previously described. Preferred arylalkyl groups containa C₁₋₄alkyl moiety. Exemplary arylalkyl groups include benzyl,2-phenethyl and naphthlenemethyl.

“Arylalkyloxy” means an arylalkyl-O— group in which the arylalkyl groupsis as previously described. Exemplary arylalkyloxy groups includebenzyloxy and 1- or 2-naphthalenemethoxy.

“Arylalkyloxycarbonyl” means an arylalkyl-O—CO— group in which thearylalkyl groups is as previously described. An exemplaryarylalkyloxycarbonyl group is benzyloxycarbonyl.

“Arylalkylthio” means an arylalkyl-S— group in which the arylalkyl groupis as previously described. An exemplary arylalkylthio group isbenzylthio.

“Arylalkynyl” means an aryl-alkynyl- group in which the aryl and alkynylare as previously described. Exemplary arylalkynyl groups includephenylethynyl and 3-phenylbut-2-ynyl.

“Aryloxy” means an aryl-O— group in which the aryl group is aspreviously described. Exemplary aryloxy groups include optionallysubstituted phenoxy and naphthoxy.

“Aryloxyalkyl” means an aryl-O-alkyl- group in which the aryl and alkylgroups are as previously described. Exemplary aryloxyalkyl groupsinclude phenoxymethyl and 1- or 2-naphthyloxymethyl.

“Aryloxycarbonyl” means an aryl-O—C(═O)— group in which the aryl groupis as previously described. Exemplary aryloxycarbonyl groups includephenoxycarbonyl and naphthoxycarbonyl.

“Arylsulfinyl” means an aryl-SO— group in which the aryl group is aspreviously described.

“Arylsulfonyl” means an aryl-SO₂— group in which the aryl group is aspreviously described.

“Arylthio” means an aryl-S— group in which the aryl group is aspreviously described. Exemplary arylthio groups include phenylthio andnaphthylthio.

“Azaheteroaryl” means an aromatic carbocyclic moiety of about 5 to about10 ring members in which one of the ring members is nitrogen and theother ring members are chosen from carbon, oxygen, sulfur, or nitrogen.Examples of azaheteroaryl groups include benzimidazolyl, imidazolyl,isoquinolinyl, isoxazolyl, pyrazolopyrimidinyl, pyridyl, pyrimidinyl,quinolinyl, quinazolinyl and thiazolyl.

“Cyclic amine” means a 3 to 8 membered monocyclic cycloalkyl ring systemwhere one of the ring carbon atoms is replaced by nitrogen and which (i)may optionally contain an additional heteroatom selected from O, S orNY³ (where Y³ is hydrogen, alkyl, arylalkyl, and aryl) and (ii) may befused to additional aryl or heteroaryl ring to form a bicyclic ringsystem. Exemplary cyclic amines include pyrrolidine, piperidine,morpholine, piperazine, indoline and pyrindoline.

“Cycloalkenyl” means a cycloalkyl group containing at least onecarbon-carbon double bond. Exemplary monocyclic cycloalkenyl ringsinclude cyclopentenyl, cyclohexenyl or cycloheptenyl.

“Cycloalkyl” means a saturated monocyclic or bicyclic ring system ofabout 3 to about 10 carbon atoms optionally substituted by oxo, alkyl,aryl or —C(═O)—NY¹Y². Exemplary monocyclic cycloalkyl rings includeC₃₋₈cycloalkyl rings such as cyclopropyl, cyclopentyl, cyclohexyl andcycloheptyl.

“Cycloalkylalkyl” means a cycloalkyl-alkyl- group in which thecycloalkyl and alkyl moieties are as previously described. Exemplarymonocyclic cycloalkylalkyl groups include cyclopropylmethyl,cyclopentylmethyl, cyclohexylmethyl and cycloheptylmethyl.

“Halo” or “halogen” means fluoro, chloro, bromo, or iodo. Preferred arefluoro or chloro.

“Heteroaroyl” means a heteroaryl-C(═O)— group in which the heteroarylgroup is as described herein. Exemplary groups include pyridylcarbonyl.

“Heteroaroylamino” means a heteroaroyl-NH— group in which the heteroarylmoiety are as previously described.

“Heteroaryl” as a group or part of a group denotes: (i) an optionallysubstituted aromatic monocyclic or multicyclic organic moiety of about 5to about 10 ring members in which one or more of the ring members is/areelement(s) other than carbon, for example nitrogen, oxygen or sulfur(examples of such groups include benzimidazolyl, benzthiazolyl,benzthiophenyl, furyl, imidazolyl, indolyl, indolizinyl, isoxazolyl,isoquinolinyl, isothiazolyl, oxadiazolyl, pyrazinyl, pyridazinyl,pyrazolyl, pyridyl, pyrimidinyl, pyrrolyl, quinazolinyl, quinolinyl,1,3,4-thiadiazolyl, thiazolyl, thienyl and triazolyl groups, optionallysubstituted by one or more aryl group substituents as defined above);(ii) an optionally substituted partially saturated multicyclicheterocarbocyclic moiety in which a heteroaryl and a cycloalkyl orcycloalkenyl group are fused together to form a cyclic structure(examples of such groups include pyrindanyl groups). Optionalsubstituents include one or more “aryl group substituents” as definedabove.

“Aryldiyl” means an optionally substituted bivalent radical derived froman aryl group as defined herein. Exemplary aryldiyl groups includeoptionally substituted phenylene, naphthylene and indanylene. Suitablesubstituents include one or more “aryl group substituents” as definedabove, particularly halogen, methyl or methoxy.

“Heteroaryldiyl” means a bivalent radical derived from a heteroarylgroup as defined below.

“Heteroarylalkenyl” means a heteroaryl-alkenyl- group in which theheteroaryl and alkenyl moieties are as previously described. Preferredheteroarylalkenyl groups contain a lower alkenyl moiety. Exemplaryheteroarylalkenyl groups include pyridylethenyl and pyridylallyl.

“Heteroarylalkyl” means a heteroaryl-alkyl- group in which theheteroaryl and alkyl moieties are as previously described. Preferredheteroarylalkyl groups contain a C₁₋₄alkyl moiety. Exemplaryheteroarylalkyl groups include pyridylmethyl.

“Heteroarylalkyloxy” means an heteroarylalkyl-O— group in which theheteroarylalkyl group is as previously described. Exemplaryheteroaryloxy groups include optionally substituted pyridylmethoxy.

“Heteroarylalkynyl” means a heteroaryl-alkynyl- group in which theheteroaryl and alkynyl moieties are as previously described. Exemplaryheteroarylalkenyl groups include pyridylethynyl and 3-pyridylbut-2-ynyl.

“Heteroaryloxy” means an heteroaryl-O— group in which the heteroarylgroup is as previously described. Exemplary heteroaryloxy groups includeoptionally substituted pyridyloxy.

“Heteroaryloxyalkyl” means an heteroaryl-O-alkyl- group in which theheteroaryl and alkyl groups are as previously described. Exemplaryheteroaryloxyalkyl groups include pyridyoxymethyl and 2-, 3- or4-quinolinyloxymethyl.

“Heterocycloalkenyl” means a cycloalkenyl group of about 3 to 7 ringmembers which contains one or more heteroatoms selected from O, S or NY⁴(where Y⁴ is hydrogen, alkyl, aryl, arylalkyl, and alkyloxycarbonyl).Exemplary heterocycloalkenyl groups include 1,2,3,6-tetrahydro-pyridine.

“Heterocycloalkyl” means: (i) a cycloalkyl group of about 3 to 7 ringmembers which contains one or more heteroatoms selected from O, S or NY⁴(where Y⁴ is hydrogen, alkyl, aryl, arylalkyl, and alkyloxycarbonyl) andwhich may optionally be substituted by oxo (examples of such groupsinclude piperidinyl, pyrrolidinyl, morpholinyl, tetrahydropyranyl andtetrahydrothiophenyl; (ii) an optionally substituted partially saturatedmulticyclic heterocarbocyclic moiety in which one or more aryl (orheteroaryl) rings and a cycloalkyl group of about 3 to 7 ring members,which contains one or more heteroatoms selected from O, S or NY⁴ andwhich may optionally be substituted by oxo, are fused together to form acyclic structure (examples of such groups include chromanyl,dihydrobenzofuranyl, indolinyl and pyrindolinyl groups).

“Heterocycloalkylalkyl” means a heterocycloalkyl-alkyl- group in whichthe heterocycloalkyl and alkyl moieties are as previously described.

“Heterocycloalkylalkyloxy” means a heterocycloalkyl-alkyl-O— group inwhich the heterocycloalkyl and alkyl moieties are as previouslydescribed.

“Heterocycloalkyloxy” means a heterocycloalkyl-O— group in which theheterocycloalkyl is as previously described.

“Prodrug” means a compound which is suitable for administration to apatient without undue toxicity, irritation, allergic response, and thelike, and is convertible in vivo by metabolic means (e.g. by hydrolysis)to a compound of the present invention, including N-oxides thereof. Athorough discussion is provided in T. Higuchi and V. Stella, Pro-drugsas Novel Delivery Systems, Vol. 14 of the A. C. S. Symposium Series, andin Edward B. Roche, ed., Bioreversible Carriers in Drug Design, AmericanPharmaceutical Association and Pergamon Press, 1987, both of which areincorporated herein by reference. For example an ester of a compound ofthe present invention containing a hydroxy group may be convertible byhydrolysis in vivo to the parent molecule. Alternatively an ester of acompound of the present invention containing a carboxy group may beconvertible by hydrolysis in vivo to the parent molecule.

Suitable esters of compounds of present invention containing a hydroxygroup, are for example acetates, citrates, lactates, tartrates,malonates, oxalates, salicylates, propionates, succinates, fumarates,maleates, methylene-bis-p-hydroxynaphthoates, gentisates, isethionates,di-p-toluoyltartrates, methanesulfonates, ethanesulfonates,benzenesulfonates, p-toluenesulfonates, cyclohexylsulfamates andquinates.

An especially useful class of esters of compounds of the presentinvention containing a hydroxy group, may be formed from acid moietiesselected from those described by Bundgaard et al., J. Med. Chem., 1989,32, page 2503-2507, and include substituted (aminomethyl)-benzoates, forexample dialkylamino-methylbenzoates in which the two alkyl groups maybe joined together and/or interrupted by an oxygen atom or by anoptionally substituted nitrogen atom, e.g. an alkylated nitrogen atom,more especially (morpholino-methyl)benzoates, e.g. 3- or4-(morpholinomethyl)-benzoates, and (4-alkylpiperazin-1-yl)benzoates,e.g. 3- or 4-(4-alkylpiperazin-1-yl)benzoates.

Suitable esters of compounds of the present invention containing acarboxy group, are for example those described by F. J. Leinweber, DrugMetab. Res., 1987, 18, page 379.

The compounds of the present invention are basic, and such compounds areuseful in the form of the free base or in the form of a pharmaceuticallyacceptable acid addition salt thereof.

Acid addition salts are a more convenient form for use; and in practice,use of the salt form inherently amounts to use of the free base form.The acids which can be used to prepare the acid addition salts includepreferably those which produce, when combined with the free base,pharmaceutically acceptable salts, that is, salts whose anions arenon-toxic to the patient in pharmaceutical doses of the salts, so thatthe beneficial inhibitory effects inherent in the free base are notvitiated by side effects ascribable to the anions. Althoughpharmaceutically acceptable salts of said basic compounds are preferred,all acid addition salts are useful as sources of the free base form evenif the particular salt, per se, is desired only as an intermediateproduct as, for example, when the salt is formed only for purposes ofpurification, and identification, or when it is used as intermediate inpreparing a pharmaceutically acceptable salt by ion exchange procedures.Pharmaceutically acceptable salts within the scope of the inventioninclude those derived from mineral acids and organic acids, and includehydrohalides, e.g. hydrochlorides and hydrobromides, sulfates,phosphates, nitrates, sulfamates, acetates, citrates, lactates,tartrates, malonates, oxalates, salicylates, propionates, succinates,fumarates, maleates, methylene-bis-b-hydroxynaphthoates, gentisates,isethionates, di-p-toluoyltartrates, methane-sulfonates,ethanesulfonates, benzenesulfonates, p-toluenesulfonates,cyclohexylsulfamates and quinates.

As well as being useful in themselves as active compounds, salts ofcompounds of the invention are useful for the purposes of purificationof the compounds, for example by exploitation of the solubilitydifferences between the salts and the parent compounds, side productsand/or starting materials by techniques well known to those skilled inthe art.

With reference to formula (Ia) above, the following are particular andpreferred groupings:

-   -   R¹ may particularly represent hydrogen.    -   R² may particularly represent hydrogen.    -   R³ may particularly represent aryl, such as optionally        substituted phenyl or optionally substituted naphthyl,        especially substituted phenyl. Exemplary optional substituents        include one or more halo atoms or alkyl substituted by aryl,        alkyl substituted by aryloxy, alkyl substituted by aroyl, alkyl        substituted by heteroaryl, arylalkynyl, heteroarylalkynyl, aryl,        heteroaryl, arylalkenyl or arylalkyloxy, in which the aryl or        heteroaryl groups may be further substituted by one or more aryl        group substituents.    -   R³ may also particularly represent heteroaryl, such as        optionally substituted pyridyl, optionally substituted        quinolinyl, optionally substituted thienyl, optionally        substituted furanyl or optionally substituted indolyl,        especially substituted thienyl, substituted pyridyl or indolyl.        Exemplary optional substituents include alkyl substituted by        aryl, alkyl substituted by aryloxy, alkyl substituted by aroyl,        alkyl substituted heteroaryl, arylalkynyl, heteroarylalkynyl,        heteroaryl, arylalkenyl or arylalkyloxy, in which the aryl or        heteroaryl groups are further substituted by one or more aryl        group substituents.    -   R⁴ may particularly represent hydrogen.    -   R⁴ may also particularly represent cyano, especially when        attached to the tertiary ring carbon atom.    -   R⁵ may particularly represent hydrogen.    -   R⁵ may also particularly represent lower alkyl (e.g. methyl) or        halo (e.g. fluoro).    -   may particularly represent a single bond.    -   n may particularly represent 2.

It is to be understood that this invention covers all appropriatecombinations of the particular and preferred groupings referred toherein.

A particular group of compounds of the invention are compounds offormula (Ib):

in which R³, R⁴ and R⁵ are as hereinbefore defined and the correspondingN-oxides, and their prodrugs; and pharmaceutically acceptable salts andsolvates (e.g. hydrates) of such compounds and their N-oxides andprodrugs.

Compounds of formula (Ib) in which R³ represents aryl, such asoptionally substituted phenyl or optionally substituted naphthyl,especially substituted phenyl, are preferred. Preferred optionalsubstituents include one or more halo atoms or alkyl substituted by arylor alkyl substituted heteroaryl, in which the aryl or heteroaryl groupsmay be further substituted by one or more aryl group substituents. R³especially represents dichlorophenyl [e.g. 3,4-dichlorophenyl],phenylC₁₋₃alkylphenyl [e.g. phenethyl], hydroxyphenylC₁₋₃alkylphenyl[e.g. 4-hydroxyphenylethylphenyl] and aminopyridylC₁₋₃alkylphenyl [e.g.(4-amino-pyrid-3-yl)ethylphenyl].

Compounds of formula (Ib) in which R³ represents heteroaryl, such asoptionally substituted pyridyl, optionally substituted quinolinyl,optionally substituted thienyl, optionally substituted furanyl oroptionally substituted indolyl, especially substituted thienyl,substituted pyridyl or indolyl, are preferred. Preferred optionalsubstituents include alkyl substituted by aryl and alkyl substitutedheteroaryl in which the aryl or heteroaryl groups are furthersubstituted by one or more aryl group substituents. R³ especiallyrepresents phenylC₁₋₃alkylpyridyl [e.g. 5-phenylethyl-pyrid-3-yl],phenylC₁₋₃alkylthienyl [e.g. 5-phenylethyl-thien-2-yl] and indolyl [e.g.indol-6-yl].

Compounds of formula (Ib) in which R⁴ represents hydrogen are preferred.

Compounds of formula (Ib) in which R⁴ represents cyano are alsopreferred. R⁴ is preferably attached at the 4 position of the piperidinering.

Compounds of formula (Ib) in which R⁵ represents hydrogen are preferred.

Compounds of formula (Ib) in which R⁵ represents lower alkyl (e.g.methyl) or halo (e.g. fluoro), are also preferred. R⁵ is preferablyattached to the phenyl ring in the position para to the —CH₂NH₂ group.

A preferred group of compounds of the invention are compounds of formula(Ib) in which: R³ is substituted phenyl [especially 3,4-dichlorophenyl,phenethyl, 4-hydroxyphenylethylphenyl and(4-amino-pyrid-3-yl)ethylphenyl] or optionally substituted heteroaryl[especially 5-phenylethyl-pyrid-3-yl, 5-phenylethyl-thien-2-yl orindol-6-yl]; R⁴ is hydrogen, or cyano attached at the 4 position of thepiperidine ring; R⁵ is hydrogen, or lower alkyl (e.g. methyl) or halo(e.g. fluoro) attached to the phenyl ring in the position para to the—CH₂NH₂ group; and the corresponding N-oxides, and their prodrugs; andpharmaceutically acceptable salts and solvates (e.g. hydrates) of suchcompounds and their N-oxides and prodrugs.

Particular compounds of the invention are selected from the compoundsformed by joining the carbon atom (C*) of one of the fragments (A1 toA12) shown in Table 1 to the carbon atom (C*) of one of the fragments(B1 to B13) shown in Table 2, and joining the nitrogen atom (N*) of oneof the fragments (B1 to B12) shown in Table 2 to the carbon atom (C*) ofone of the acidic fragments (C1 to C140) depicted in Table 3. TABLE 1 A1

A2

A3

A4

A5

A6

A7

A8

A9

A10

A11

A12

TABLE 2 B1

B2

B3

B4

B5

B6

B7

B8

B9

B10

B11

B12

B13

TABLE 3 C1

C2

C3

C4

C5

C6

C7

C8

C9

C10

C11

C12

C13

C14

C15

C16

C17

C18

C19

C20

C21

C22

C23

C24

C25

C26

C27

C28

C29

C30

C31

C32

C33

C34

C35

C36

C37

C38

C39

C40

C41

C42

C43

C44

C45

C46

C47

C48

C49

C50

C51

C52

C53

C54

C55

C56

C57

C58

C59

C60

C61

C62

C63

C64

C65

C66

C67

C68

C69

C70

C71

C72

C73

C74

C75

C76

C77

C78

C79

C80

C81

C82

C83

C84

C85

C86

C87

C88

C89

C90

C91

C92

C93

C94

C95

C96

C97

C98

C99

C100

C101

C102

C103

C104

C105

C106

C107

C108

C109

C110

C111

C112

C113

C114

C115

C116

C117

C118

C119

C120

C121

C122

C123

C124

C125

C126

C127

C128

C129

C130

C131

C132

C133

C134

C135

C136

C137

C138

C139

C140

Particularly preferred examples of fragments “A”, “B”, and “C” areillustrated in Table 4 below: TABLE 4 A1-B1-C1 A1-B1-C2 A1-B1-C3A1-B1-C4 A1-B1-C5 A1-B1-C6 A1-B1-C7 A1-B1-C8 A1-B1-C9 A1-B1-C10A1-B1-C11 A1-B1-C12 A1-B1-C13 A1-B1-C14 A1-B1-C15 A1-B1-C16 A1-B1-C17A1-B1-C18 A1-B1-C19 A1-B1-C20 A1-B1-C21 A1-B1-C22 A1-B1-C23 A1-B1-C24A1-B1-C25 A1-B1-C26 A1-B1-C27 A1-B1-C28 A1-B1-C29 A1-B1-C30 A1-B1-C31A1-B1-C32 A1-B1-C33 A1-B1-C34 A1-B1-C35 A1-B1-C36 A1-B1-C37 A1-B1-C38A1-B1-C39 A1-B1-C40 A1-B1-C41 A1-B1-C42 A1-B1-C43 A1-B1-C44 A1-B1-C45A1-B1-C46 A1-B1-C47 A1-B1-C48 A1-B1-C49 A1-B1-C50 A1-B1-C51 A1-B1-C52A1-B1-C53 A1-B1-C54 A1-B1-C55 A1-B1-C56 A1-B1-C57 A1-B1-C58 A1-B1-C59A1-B1-C60 A1-B1-C61 A1-B1-C62 A1-B1-C63 A1-B1-C64 A1-B1-C65 A1-B1-C66A1-B1-C67 A1-B1-C68 A1-B1-C69 A1-B1-C70 A1-B1-C71 A1-B1-C72 A1-B1-C73A1-B1-C74 A1-B1-C75 A1-B1-C76 A1-B1-C77 A1-B1-C78 A1-B1-C79 A1-B1-C80A1-B1-C81 A1-B1-C82 A1-B1-C83 A1-B1-C84 A1-B1-C85 A1-B1-C86 A1-B1-C87A1-B1-C88 A1-B1-C89 A1-B1-C90 A1-B1-C91 A1-B1-C92 A1-B1-C93 A1-B1-C94A1-B1-C95 A1-B1-C96 A1-B1-C97 A1-B1-C98 A1-B1-C99 A1-B1-C100 A1-B1-C101A1-B1-C102 A1-B1-C103 A1-B1-C104 A1-B1-C105 A1-B1-C106 A1-B1-C107A1-B1-C108 A1-B1-C109 A1-B1-C110 A1-B1-C111 A1-B1-C112 A1-B1-C113A1-B1-C114 A1-B1-C115 A1-B1-C116 A1-B1-C117 A1-B1-C118 A1-B1-C119A1-B1-C120 A1-B1-C121 A1-B1-C122 A1-B1-C123 A1-B1-C124 A1-B1-C125A1-B1-C126 A1-B1-C127 A1-B1-C128 A1-B1-C129 A1-B1-C130 A1-B1-C131A1-B1-C132 A1-B1-C133 A1-B1-C134 A1-B1-C135 A1-B1-C136 A1-B1-C137A1-B1-C138 A1-B1-C139 A1-B1-C140 BLANK BLANK BLANK BLANK A1-B2-C1A1-B2-C2 A1-B2-C3 A1-B2-C4 A1-B2-C5 A1-B2-C6 A1-B2-C7 A1-B2-C8 A1-B2-C9A1-B2-C10 A1-B2-C11 A1-B2-C12 A1-B2-C13 A1-B2-C14 A1-B2-C15 A1-B2-C16A1-B2-C17 A1-B2-C18 A1-B2-C19 A1-B2-C20 A1-B2-C21 A1-B2-C22 A1-B2-C23A1-B2-C24 A1-B2-C25 A1-B2-C26 A1-B2-C27 A1-B2-C28 A1-B2-C29 A1-B2-C30A1-B2-C31 A1-B2-C32 A1-B2-C33 A1-B2-C34 A1-B2-C35 A1-B2-C36 A1-B2-C37A1-B2-C38 A1-B2-C39 A1-B2-C40 A1-B2-C41 A1-B2-C42 A1-B2-C43 A1-B2-C44A1-B2-C45 A1-B2-C46 A1-B2-C47 A1-B2-C48 A1-B2-C49 A1-B2-C50 A1-B2-C51A1-B2-C52 A1-B2-C53 A1-B2-C54 A1-B2-C55 A1-B2-C56 A1-B2-C57 A1-B2-C58A1-B2-C59 A1-B2-C60 A1-B2-C61 A1-B2-C62 A1-B2-C63 A1-B2-C64 A1-B2-C65A1-B2-C66 A1-B2-C67 A1-B2-C68 A1-B2-C69 A1-B2-C70 A1-B2-C71 A1-B2-C72A1-B2-C73 A1-B2-C74 A1-B2-C75 A1-B2-C76 A1-B2-C77 A1-B2-C78 A1-B2-C79A1-B2-C80 A1-B2-C81 A1-B2-C82 A1-B2-C83 A1-B2-C84 A1-B2-C85 A1-B2-C86A1-B2-C87 A1-B2-C88 A1-B2-C89 A1-B2-C90 A1-B2-C91 A1-B2-C92 A1-B2-C93A1-B2-C94 A1-B2-C95 A1-B2-C96 A1-B2-C97 A1-B2-C98 A1-B2-C99 A1-B2-C100A1-B2-C101 A1-B2-C102 A1-B2-C103 A1-B2-C104 A1-B2-C105 A1-B2-C106A1-B2-C107 A1-B2-C108 A1-B2-C109 A1-B2-C110 A1-B2-C111 A1-B2-C112A1-B2-C113 A1-B2-C114 A1-B2-C115 A1-B2-C116 A1-B2-C117 A1-B2-C118A1-B2-C119 A1-B2-C120 A1-B2-C121 A1-B2-C122 A1-B2-C123 A1-B2-C124A1-B2-C125 A1-B2-C126 A1-B2-C127 A1-B2-C128 A1-B2-C129 A1-B2-C130A1-B2-C131 A1-B2-C132 A1-B2-C133 A1-B2-C134 A1-B2-C135 A1-B2-C136A1-B2-C137 A1-B2-C138 A1-B2-C139 A1-B2-C140 BLANK BLANK BLANK BLANKA1-B3-C1 A1-B3-C2 A1-B3-C3 A1-B3-C4 A1-B3-C5 A1-B3-C6 A1-B3-C7 A1-B3-C8A1-B3-C9 A1-B3-C10 A1-B3-C11 A1-B3-C12 A1-B3-C13 A1-B3-C14 A1-B3-C15A1-B3-C16 A1-B3-C17 A1-B3-C18 A1-B3-C19 A1-B3-C20 A1-B3-C21 A1-B3-C22A1-B3-C23 A1-B3-C24 A1-B3-C25 A1-B3-C26 A1-B3-C27 A1-B3-C28 A1-B3-C29A1-B3-C30 A1-B3-C31 A1-B3-C32 A1-B3-C33 A1-B3-C34 A1-B3-C35 A1-B3-C36A1-B3-C37 A1-B3-C38 A1-B3-C39 A1-B3-C40 A1-B3-C41 A1-B3-C42 A1-B3-C43A1-B3-C44 A1-B3-C45 A1-B3-C46 A1-B3-C47 A1-B3-C48 A1-B3-C49 A1-B3-C50A1-B3-C51 A1-B3-C52 A1-B3-C53 A1-B3-C54 A1-B3-C55 A1-B3-C56 A1-B3-C57A1-B3-C58 A1-B3-C59 A1-B3-C60 A1-B3-C61 A1-B3-C62 A1-B3-C63 A1-B3-C64A1-B3-C65 A1-B3-C66 A1-B3-C67 A1-B3-C68 A1-B3-C69 A1-B3-C70 A1-B3-C71A1-B3-C72 A1-B3-C73 A1-B3-C74 A1-B3-C75 A1-B3-C76 A1-B3-C77 A1-B3-C78A1-B3-C79 A1-B3-C80 A1-B3-C81 A1-B3-C82 A1-B3-C83 A1-B3-C84 A1-B3-C85A1-B3-C86 A1-B3-C87 A1-B3-C88 A1-B3-C89 A1-B3-C90 A1-B3-C91 A1-B3-C92A1-B3-C93 A1-B3-C94 A1-B3-C95 A1-B3-C96 A1-B3-C97 A1-B3-C98 A1-B3-C99A1-B3-C100 A1-B3-C101 A1-B3-C102 A1-B3-C103 A1-B3-C104 A1-B3-C105A1-B3-C106 A1-B3-C107 A1-B3-C108 A1-B3-C109 A1-B3-C110 A1-B3-C111A1-B3-C112 A1-B3-C113 A1-B3-C114 A1-B3-C115 A1-B3-C116 A1-B3-C117A1-B3-C118 A1-B3-C119 A1-B3-C120 A1-B3-C121 A1-B3-C122 A1-B3-C123A1-B3-C124 A1-B3-C125 A1-B3-C126 A1-B3-C127 A1-B3-C128 A1-B3-C129A1-B3-C130 A1-B3-C131 A1-B3-C132 A1-B3-C133 A1-B3-C134 A1-B3-C135A1-B3-C136 A1-B3-C137 A1-B3-C138 A1-B3-C139 A1-B3-C140 BLANK BLANK BLANKBLANK A1-B4-C1 A1-B4-C2 A1-B4-C3 A1-B4-C4 A1-B4-C5 A1-B4-C6 A1-B4-C7A1-B4-C8 A1-B4-C9 A1-B4-C10 A1-B4-C11 A1-B4-C12 A1-B4-C13 A1-B4-C14A1-B4-C15 A1-B4-C16 A1-B4-C17 A1-B4-C18 A1-B4-C19 A1-B4-C20 A1-B4-C21A1-B4-C22 A1-B4-C23 A1-B4-C24 A1-B4-C25 A1-B4-C26 A1-B4-C27 A1-B4-C28A1-B4-C29 A1-B4-C30 A1-B4-C31 A1-B4-C32 A1-B4-C33 A1-B4-C34 A1-B4-C35A1-B4-C36 A1-B4-C37 A1-B4-C38 A1-B4-C39 A1-B4-C40 A1-B4-C41 A1-B4-C42A1-B4-C43 A1-B4-C44 A1-B4-C45 A1-B4-C46 A1-B4-C47 A1-B4-C48 A1-B4-C49A1-B4-C50 A1-B4-C51 A1-B4-C52 A1-B4-C53 A1-B4-C54 A1-B4-C55 A1-B4-C56A1-B4-C57 A1-B4-C58 A1-B4-C59 A1-B4-C60 A1-B4-C61 A1-B4-C62 A1-B4-C63A1-B4-C64 A1-B4-C65 A1-B4-C66 A1-B4-C67 A1-B4-C68 A1-B4-C69 A1-B4-C70A1-B4-C71 A1-B4-C72 A1-B4-C73 A1-B4-C74 A1-B4-C75 A1-B4-C76 A1-B4-C77A1-B4-C78 A1-B4-C79 A1-B4-C80 A1-B4-C81 A1-B4-C82 A1-B4-C83 A1-B4-C84A1-B4-C85 A1-B4-C86 A1-B4-C87 A1-B4-C88 A1-B4-C89 A1-B4-C90 A1-B4-C91A1-B4-C92 A1-B4-C93 A1-B4-C94 A1-B4-C95 A1-B4-C96 A1-B4-C97 A1-B4-C98A1-B4-C99 A1-B4-C100 A1-B4-C101 A1-B4-C102 A1-B4-C103 A1-B4-C104A1-B4-C105 A1-B4-C106 A1-B4-C107 A1-B4-C108 A1-B4-C109 A1-B4-C110A1-B4-C111 A1-B4-C112 A1-B4-C113 A1-B4-C114 A1-B4-C115 A1-B4-C116A1-B4-C117 A1-B4-C118 A1-B4-C119 A1-B4-C120 A1-B4-C121 A1-B4-C122A1-B4-C123 A1-B4-C124 A1-B4-C125 A1-B4-C126 A1-B4-C127 A1-B4-C128A1-B4-C129 A1-B4-C130 A1-B4-C131 A1-B4-C132 A1-B4-C133 A1-B4-C134A1-B4-C135 A1-B4-C136 A1-B4-C137 A1-B4-C138 A1-B4-C139 A1-B4-C140 BLANKBLANK BLANK BLANK A1-B5-C1 A1-B5-C2 A1-B5-C3 A1-B5-C4 A1-B5-C5 A1-B5-C6A1-B5-C7 A1-B5-C8 A1-B5-C9 A1-B5-C10 A1-B5-C11 A1-B5-C12 A1-B5-C13A1-B5-C14 A1-B5-C15 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A9-B12-C138A9-B12-C139 A9-B12-C140 BLANK BLANK BLANK BLANK A9-B13-C1 A9-B13-C2A9-B13-C3 A9-B13-C4 A9-B13-C5 A9-B13-C6 A9-B13-C7 A9-B13-C8 A9-B13-C9A9-B13-C10 A9-B13-C11 A9-B13-C12 A9-B13-C13 A9-B13-C14 A9-B13-C15A9-B13-C16 A9-B13-C17 A9-B13-C18 A9-B13-C19 A9-B13-C20 A9-B13-C21A9-B13-C22 A9-B13-C23 A9-B13-C24 A9-B13-C25 A9-B13-C26 A9-B13-C27A9-B13-C28 A9-B13-C29 A9-B13-C30 A9-B13-C31 A9-B13-C32 A9-B13-C33A9-B13-C34 A9-B13-C35 A9-B13-C36 A9-B13-C37 A9-B13-C38 A9-B13-C39A9-B13-C40 A9-B13-C41 A9-B13-C42 A9-B13-C43 A9-B13-C44 A9-B13-C45A9-B13-C46 A9-B13-C47 A9-B13-C48 A9-B13-C49 A9-B13-C50 A9-B13-C51A9-B13-C52 A9-B13-C53 A9-B13-C54 A9-B13-C55 A9-B13-C56 A9-B13-C57A9-B13-C58 A9-B13-C59 A9-B13-C60 A9-B13-C61 A9-B13-C62 A9-B13-C63A9-B13-C64 A9-B13-C65 A9-B13-C66 A9-B13-C67 A9-B13-C68 A9-B13-C69A9-B13-C70 A9-B13-C71 A9-B13-C72 A9-B13-C73 A9-B13-C74 A9-B13-C75A9-B13-C76 A9-B13-C77 A9-B13-C78 A9-B13-C79 A9-B13-C80 A9-B13-C81A9-B13-C82 A9-B13-C83 A9-B13-C84 A9-B13-C85 A9-B13-C86 A9-B13-C87A9-B13-C88 A9-B13-C89 A9-B13-C90 A9-B13-C91 A9-B13-C92 A9-B13-C93A9-B13-C94 A9-B13-C95 A9-B13-C96 A9-B13-C97 A9-B13-C98 A9-B13-C99A9-B13-C100 A9-B13-C101 A9-B13-C102 A9-B13-C103 A9-B13-C104 A9-B13-C105A9-B13-C106 A9-B13-C107 A9-B13-C108 A9-B13-C109 A9-B13-C110 A9-B13-C111A9-B13-C112 A9-B13-C113 A9-B13-C114 A9-B13-C115 A9-B13-C116 A9-B13-C117A9-B13-C118 A9-B13-C119 A9-B13-C120 A9-B13-C121 A9-B13-C122 A9-B13-C123A9-B13-C124 A9-B13-C125 A9-B13-C126 A9-B13-C127 A9-B13-C128 A9-B13-C129A9-B13-C130 A9-B13-C131 A9-B13-C132 A9-B13-C133 A9-B13-C134 A9-B13-C135A9-B13-C136 A9-B13-C137 A9-B13-C138 A9-B13-C139 A9-B13-C140 BLANK BLANKBLANK BLANK A10-B1-C1 A10-B1-C2 A10-B1-C3 A10-B1-C4 A10-B1-C5 A10-B1-C6A10-B1-C7 A10-B1-C8 A10-B1-C9 A10-B1-C10 A10-B1-C11 A10-B1-C12A10-B1-C13 A10-B1-C14 A10-B1-C15 A10-B1-C16 A10-B1-C17 A10-B1-C18A10-B1-C19 A10-B1-C20 A10-B1-C21 A10-B1-C22 A10-B1-C23 A10-B1-C24A10-B1-C25 A10-B1-C26 A10-B1-C27 A10-B1-C28 A10-B1-C29 A10-B1-C30A10-B1-C31 A10-B1-C32 A10-B1-C33 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A10-B1-C124 A10-B1-C125 A10-B1-C126A10-B1-C127 A10-B1-C128 A10-B1-C129 A10-B1-C130 A10-B1-C131 A10-B1-C132A10-B1-C133 A10-B1-C134 A10-B1-C135 A10-B1-C136 A10-B1-C137 A10-B1-C138A10-B1-C139 A10-B1-C140 BLANK BLANK BLANK BLANK A10-B2-C1 A10-B2-C2A10-B2-C3 A10-B2-C4 A10-B2-C5 A10-B2-C6 A10-B2-C7 A10-B2-C8 A10-B2-C9A10-B2-C10 A10-B2-C11 A10-B2-C12 A10-B2-C13 A10-B2-C14 A10-B2-C15A10-B2-C16 A10-B2-C17 A10-B2-C18 A10-B2-C19 A10-B2-C20 A10-B2-C21A10-B2-C22 A10-B2-C23 A10-B2-C24 A10-B2-C25 A10-B2-C26 A10-B2-C27A10-B2-C28 A10-B2-C29 A10-B2-C30 A10-B2-C31 A10-B2-C32 A10-B2-C33A10-B2-C34 A10-B2-C35 A10-B2-C36 A10-B2-C37 A10-B2-C38 A10-B2-C39A10-B2-C40 A10-B2-C41 A10-B2-C42 A10-B2-C43 A10-B2-C44 A10-B2-C45A10-B2-C46 A10-B2-C47 A10-B2-C48 A10-B2-C49 A10-B2-C50 A10-B2-C51A10-B2-C52 A10-B2-C53 A10-B2-C54 A10-B2-C55 A10-B2-C56 A10-B2-C57A10-B2-C58 A10-B2-C59 A10-B2-C60 A10-B2-C61 A10-B2-C62 A10-B2-C63A10-B2-C64 A10-B2-C65 A10-B2-C66 A10-B2-C67 A10-B2-C68 A10-B2-C69A10-B2-C70 A10-B2-C71 A10-B2-C72 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A10-B7-C82 A10-B7-C83 A10-B7-C84A10-B7-C85 A10-B7-C86 A10-B7-C87 A10-B7-C88 A10-B7-C89 A10-B7-C90A10-B7-C91 A10-B7-C92 A10-B7-C93 A10-B7-C94 A10-B7-C95 A10-B7-C96A10-B7-C97 A10-B7-C98 A10-B7-C99 A10-B7-C100 A10-B7-C101 A10-B7-C102A10-B7-C103 A10-B7-C104 A10-B7-C105 A10-B7-C106 A10-B7-C107 A10-B7-C108A10-B7-C109 A10-B7-C110 A10-B7-C111 A10-B7-C112 A10-B7-C113 A10-B7-C114A10-B7-C115 A10-B7-C116 A10-B7-C117 A10-B7-C118 A10-B7-C119 A10-B7-C120A10-B7-C121 A10-B7-C122 A10-B7-C123 A10-B7-C124 A10-B7-C125 A10-B7-C126A10-B7-C127 A10-B7-C128 A10-B7-C129 A10-B7-C130 A10-B7-C131 A10-B7-C132A10-B7-C133 A10-B7-C134 A10-B7-C135 A10-B7-C136 A10-B7-C137 A10-B7-C138A10-B7-C139 A10-B7-C140 BLANK BLANK BLANK BLANK A10-B8-C1 A10-B8-C2A10-B8-C3 A10-B8-C4 A10-B8-C5 A10-B8-C6 A10-B8-C7 A10-B8-C8 A10-B8-C9A10-B8-C10 A10-B8-C11 A10-B8-C12 A10-B8-C13 A10-B8-C14 A10-B8-C15A10-B8-C16 A10-B8-C17 A10-B8-C18 A10-B8-C19 A10-B8-C20 A10-B8-C21A10-B8-C22 A10-B8-C23 A10-B8-C24 A10-B8-C25 A10-B8-C26 A10-B8-C27A10-B8-C28 A10-B8-C29 A10-B8-C30 A10-B8-C31 A10-B8-C32 A10-B8-C33A10-B8-C34 A10-B8-C35 A10-B8-C36 A10-B8-C37 A10-B8-C38 A10-B8-C39A10-B8-C40 A10-B8-C41 A10-B8-C42 A10-B8-C43 A10-B8-C44 A10-B8-C45A10-B8-C46 A10-B8-C47 A10-B8-C48 A10-B8-C49 A10-B8-C50 A10-B8-C51A10-B8-C52 A10-B8-C53 A10-B8-C54 A10-B8-C55 A10-B8-C56 A10-B8-C57A10-B8-C58 A10-B8-C59 A10-B8-C60 A10-B8-C61 A10-B8-C62 A10-B8-C63A10-B8-C64 A10-B8-C65 A10-B8-C66 A10-B8-C67 A10-B8-C68 A10-B8-C69A10-B8-C70 A10-B8-C71 A10-B8-C72 A10-B8-C73 A10-B8-C74 A10-B8-C75A10-B8-C76 A10-B8-C77 A10-B8-C78 A10-B8-C79 A10-B8-C80 A10-B8-C81A10-B8-C82 A10-B8-C83 A10-B8-C84 A10-B8-C85 A10-B8-C86 A10-B8-C87A10-B8-C88 A10-B8-C89 A10-B8-C90 A10-B8-C91 A10-B8-C92 A10-B8-C93A10-B8-C94 A10-B8-C95 A10-B8-C96 A10-B8-C97 A10-B8-C98 A10-B8-C99A10-B8-C100 A10-B8-C101 A10-B8-C102 A10-B8-C103 A10-B8-C104 A10-B8-C105A10-B8-C106 A10-B8-C107 A10-B8-C108 A10-B8-C109 A10-B8-C110 A10-B8-C111A10-B8-C112 A10-B8-C113 A10-B8-C114 A10-B8-C115 A10-B8-C116 A10-B8-C117A10-B8-C118 A10-B8-C119 A10-B8-C120 A10-B8-C121 A10-B8-C122 A10-B8-C123A10-B8-C124 A10-B8-C125 A10-B8-C126 A10-B8-C127 A10-B8-C128 A10-B8-C129A10-B8-C130 A10-B8-C131 A10-B8-C132 A10-B8-C133 A10-B8-C134 A10-B8-C135A10-B8-C136 A10-B8-C137 A10-B8-C138 A10-B8-C139 A10-B8-C140 BLANK BLANKBLANK BLANK A10-B9-C1 A10-B9-C2 A10-B9-C3 A10-B9-C4 A10-B9-C5 A10-B9-C6A10-B9-C7 A10-B9-C8 A10-B9-C9 A10-B9-C10 A10-B9-C11 A10-B9-C12A10-B9-C13 A10-B9-C14 A10-B9-C15 A10-B9-C16 A10-B9-C17 A10-B9-C18A10-B9-C19 A10-B9-C20 A10-B9-C21 A10-B9-C22 A10-B9-C23 A10-B9-C24A10-B9-C25 A10-B9-C26 A10-B9-C27 A10-B9-C28 A10-B9-C29 A10-B9-C30A10-B9-C31 A10-B9-C32 A10-B9-C33 A10-B9-C34 A10-B9-C35 A10-B9-C36A10-B9-C37 A10-B9-C38 A10-B9-C39 A10-B9-C40 A10-B9-C41 A10-B9-C42A10-B9-C43 A10-B9-C44 A10-B9-C45 A10-B9-C46 A10-B9-C47 A10-B9-C48A10-B9-C49 A10-B9-C50 A10-B9-C51 A10-B9-C52 A10-B9-C53 A10-B9-C54A10-B9-C55 A10-B9-C56 A10-B9-C57 A10-B9-C58 A10-B9-C59 A10-B9-C60A10-B9-C61 A10-B9-C62 A10-B9-C63 A10-B9-C64 A10-B9-C65 A10-B9-C66A10-B9-C67 A10-B9-C68 A10-B9-C69 A10-B9-C70 A10-B9-C71 A10-B9-C72A10-B9-C73 A10-B9-C74 A10-B9-C75 A10-B9-C76 A10-B9-C77 A10-B9-C78A10-B9-C79 A10-B9-C80 A10-B9-C81 A10-B9-C82 A10-B9-C83 A10-B9-C84A10-B9-C85 A10-B9-C86 A10-B9-C87 A10-B9-C88 A10-B9-C89 A10-B9-C90A10-B9-C91 A10-B9-C92 A10-B9-C93 A10-B9-C94 A10-B9-C95 A10-B9-C96A10-B9-C97 A10-B9-C98 A10-B9-C99 A10-B9-C100 A10-B9-C101 A10-B9-C102A10-B9-C103 A10-B9-C104 A10-B9-C105 A10-B9-C106 A10-B9-C107 A10-B9-C108A10-B9-C109 A10-B9-C110 A10-B9-C111 A10-B9-C112 A10-B9-C113 A10-B9-C114A10-B9-C115 A10-B9-C116 A10-B9-C117 A10-B9-C118 A10-B9-C119 A10-B9-C120A10-B9-C121 A10-B9-C122 A10-B9-C123 A10-B9-C124 A10-B9-C125 A10-B9-C126A10-B9-C127 A10-B9-C128 A10-B9-C129 A10-B9-C130 A10-B9-C131 A10-B9-C132A10-B9-C133 A10-B9-C134 A10-B9-C135 A10-B9-C136 A10-B9-C137 A10-B9-C138A10-B9-C139 A10-B9-C140 BLANK BLANK BLANK BLANK A10-B10-C1 A10-B10-C2A10-B10-C3 A10-B10-C4 A10-B10-C5 A10-B10-C6 A10-B10-C7 A10-B10-C8A10-B10-C9 A10-B10-C10 A10-B10-C11 A10-B10-C12 A10-B10-C13 A10-B10-C14A10-B10-C15 A10-B10-C16 A10-B10-C17 A10-B10-C18 A10-B10-C19 A10-B10-C20A10-B10-C21 A10-B10-C22 A10-B10-C23 A10-B10-C24 A10-B10-C25 A10-B10-C26A10-B10-C27 A10-B10-C28 A10-B10-C29 A10-B10-C30 A10-B10-C31 A10-B10-C32A10-B10-C33 A10-B10-C34 A10-B10-C35 A10-B10-C36 A10-B10-C37 A10-B10-C38A10-B10-C39 A10-B10-C40 A10-B10-C41 A10-B10-C42 A10-B10-C43 A10-B10-C44A10-B10-C45 A10-B10-C46 A10-B10-C47 A10-B10-C48 A10-B10-C49 A10-B10-C50A10-B10-C51 A10-B10-C52 A10-B10-C53 A10-B10-C54 A10-B10-C55 A10-B10-C56A10-B10-C57 A10-B10-C58 A10-B10-C59 A10-B10-C60 A10-B10-C61 A10-B10-C62A10-B10-C63 A10-B10-C64 A10-B10-C65 A10-B10-C66 A10-B10-C67 A10-B10-C68A10-B10-C69 A10-B10-C70 A10-B10-C71 A10-B10-C72 A10-B10-C73 A10-B10-C74A10-B10-C75 A10-B10-C76 A10-B10-C77 A10-B10-C78 A10-B10-C79 A10-B10-C80A10-B10-C81 A10-B10-C82 A10-B10-C83 A10-B10-C84 A10-B10-C85 A10-B10-C86A10-B10-C87 A10-B10-C88 A10-B10-C89 A10-B10-C90 A10-B10-C91 A10-B10-C92A10-B10-C93 A10-B10-C94 A10-B10-C95 A10-B10-C96 A10-B10-C97 A10-B10-C98A10-B10-C99 A10-B10-C100 A10-B10-C101 A10-B10-C102 A10-B10-C103A10-B10-C104 A10-B10-C105 A10-B10-C106 A10-B10-C107 A10-B10-C108A10-B10-C109 A10-B10-C110 A10-B10-C111 A10-B10-C112 A10-B10-C113A10-B10-C114 A10-B10-C115 A10-B10-C116 A10-B10-C117 A10-B10-C118A10-B10-C119 A10-B10-C120 A10-B10-C121 A10-B10-C122 A10-B10-C123A10-B10-C124 A10-B10-C125 A10-B10-C126 A10-B10-C127 A10-B10-C128A10-B10-C129 A10-B10-C130 A10-B10-C131 A10-B10-C132 A10-B10-C133A10-B10-C134 A10-B10-C135 A10-B10-C136 A10-B10-C137 A10-B10-C138A10-B10-C139 A10-B10-C140 BLANK BLANK BLANK BLANK A10-B11-C1 A10-B11-C2A10-B11-C3 A10-B11-C4 A10-B11-C5 A10-B11-C6 A10-B11-C7 A10-B11-C8A10-B11-C9 A10-B11-C10 A10-B11-C11 A10-B11-C12 A10-B11-C13 A10-B11-C14A10-B11-C15 A10-B11-C16 A10-B11-C17 A10-B11-C18 A10-B11-C19 A10-B11-C20A10-B11-C21 A10-B11-C22 A10-B11-C23 A10-B11-C24 A10-B11-C25 A10-B11-C26A10-B11-C27 A10-B11-C28 A10-B11-C29 A10-B11-C30 A10-B11-C31 A10-B11-C32A10-B11-C33 A10-B11-C34 A10-B11-C35 A10-B11-C36 A10-B11-C37 A10-B11-C38A10-B11-C39 A10-B11-C40 A10-B11-C41 A10-B11-C42 A10-B11-C43 A10-B11-C44A10-B11-C45 A10-B11-C46 A10-B11-C47 A10-B11-C48 A10-B11-C49 A10-B11-C50A10-B11-C51 A10-B11-C52 A10-B11-C53 A10-B11-C54 A10-B11-C55 A10-B11-C56A10-B11-C57 A10-B11-C58 A10-B11-C59 A10-B11-C60 A10-B11-C61 A10-B11-C62A10-B11-C63 A10-B11-C64 A10-B11-C65 A10-B11-C66 A10-B11-C67 A10-B11-C68A10-B11-C69 A10-B11-C70 A10-B11-C71 A10-B11-C72 A10-B11-C73 A10-B11-C74A10-B11-C75 A10-B11-C76 A10-B11-C77 A10-B11-C78 A10-B11-C79 A10-B11-C80A10-B11-C81 A10-B11-C82 A10-B11-C83 A10-B11-C84 A10-B11-C85 A10-B11-C86A10-B11-C87 A10-B11-C88 A10-B11-C89 A10-B11-C90 A10-B11-C91 A10-B11-C92A10-B11-C93 A10-B11-C94 A10-B11-C95 A10-B11-C96 A10-B11-C97 A10-B11-C98A10-B11-C99 A10-B11-C100 A10-B11-C101 A10-B11-C102 A10-B11-C103A10-B11-C104 A10-B11-C105 A10-B11-C106 A10-B11-C107 A10-B11-C108A10-B11-C109 A10-B11-C110 A10-B11-C111 A10-B11-C112 A10-B11-C113A10-B11-C114 A10-B11-C115 A10-B11-C116 A10-B11-C117 A10-B11-C118A10-B11-C119 A10-B11-C120 A10-B11-C121 A10-B11-C122 A10-B11-C123A10-B11-C124 A10-B11-C125 A10-B11-C126 A10-B11-C127 A10-B11-C128A10-B11-C129 A10-B11-C130 A10-B11-C131 A10-B11-C132 A10-B11-C133A10-B11-C134 A10-B11-C135 A10-B11-C136 A10-B11-C137 A10-B11-C138A10-B11-C139 A10-B11-C140 BLANK BLANK BLANK BLANK A10-B12-C1 A10-B12-C2A10-B12-C3 A10-B12-C4 A10-B12-C5 A10-B12-C6 A10-B12-C7 A10-B12-C8A10-B12-C9 A10-B12-C10 A10-B12-C11 A10-B12-C12 A10-B12-C13 A10-B12-C14A10-B12-C15 A10-B12-C16 A10-B12-C17 A10-B12-C18 A10-B12-C19 A10-B12-C20A10-B12-C21 A10-B12-C22 A10-B12-C23 A10-B12-C24 A10-B12-C25 A10-B12-C26A10-B12-C27 A10-B12-C28 A10-B12-C29 A10-B12-C30 A10-B12-C31 A10-B12-C32A10-B12-C33 A10-B12-C34 A10-B12-C35 A10-B12-C36 A10-B12-C37 A10-B12-C38A10-B12-C39 A10-B12-C40 A10-B12-C41 A10-B12-C42 A10-B12-C43 A10-B12-C44A10-B12-C45 A10-B12-C46 A10-B12-C47 A10-B12-C48 A10-B12-C49 A10-B12-C50A10-B12-C51 A10-B12-C52 A10-B12-C53 A10-B12-C54 A10-B12-C55 A10-B12-C56A10-B12-C57 A10-B12-C58 A10-B12-C59 A10-B12-C60 A10-B12-C61 A10-B12-C62A10-B12-C63 A10-B12-C64 A10-B12-C65 A10-B12-C66 A10-B12-C67 A10-B12-C68A10-B12-C69 A10-B12-C70 A10-B12-C71 A10-B12-C72 A10-B12-C73 A10-B12-C74A10-B12-C75 A10-B12-C76 A10-B12-C77 A10-B12-C78 A10-B12-C79 A10-B12-C80A10-B12-C81 A10-B12-C82 A10-B12-C83 A10-B12-C84 A10-B12-C85 A10-B12-C86A10-B12-C87 A10-B12-C88 A10-B12-C89 A10-B12-C90 A10-B12-C91 A10-B12-C92A10-B12-C93 A10-B12-C94 A10-B12-C95 A10-B12-C96 A10-B12-C97 A10-B12-C98A10-B12-C99 A10-B12-C100 A10-B12-C101 A10-B12-C102 A10-B12-C103A10-B12-C104 A10-B12-C105 A10-B12-C106 A10-B12-C107 A10-B12-C108A10-B12-C109 A10-B12-C110 A10-B12-C111 A10-B12-C112 A10-B12-C113A10-B12-C114 A10-B12-C115 A10-B12-C116 A10-B12-C117 A10-B12-C118A10-B12-C119 A10-B12-C120 A10-B12-C121 A10-B12-C122 A10-B12-C123A10-B12-C124 A10-B12-C125 A10-B12-C126 A10-B12-C127 A10-B12-C128A10-B12-C129 A10-B12-C130 A10-B12-C131 A10-B12-C132 A10-B12-C133A10-B12-C134 A10-B12-C135 A10-B12-C136 A10-B12-C137 A10-B12-C138A10-B12-C139 A10-B12-C140 BLANK BLANK BLANK BLANK A10-B13-C1 A10-B13-C2A10-B13-C3 A10-B13-C4 A10-B13-C5 A10-B13-C6 A10-B13-C7 A10-B13-C8A10-B13-C9 A10-B13-C10 A10-B13-C11 A10-B13-C12 A10-B13-C13 A10-B13-C14A10-B13-C15 A10-B13-C16 A10-B13-C17 A10-B13-C18 A10-B13-C19 A10-B13-C20A10-B13-C21 A10-B13-C22 A10-B13-C23 A10-B13-C24 A10-B13-C25 A10-B13-C26A10-B13-C27 A10-B13-C28 A10-B13-C29 A10-B13-C30 A10-B13-C31 A10-B13-C32A10-B13-C33 A10-B13-C34 A10-B13-C35 A10-B13-C36 A10-B13-C37 A10-B13-C38A10-B13-C39 A10-B13-C40 A10-B13-C41 A10-B13-C42 A10-B13-C43 A10-B13-C44A10-B13-C45 A10-B13-C46 A10-B13-C47 A10-B13-C48 A10-B13-C49 A10-B13-C50A10-B13-C51 A10-B13-C52 A10-B13-C53 A10-B13-C54 A10-B13-C55 A10-B13-C56A10-B13-C57 A10-B13-C58 A10-B13-C59 A10-B13-C60 A10-B13-C61 A10-B13-C62A10-B13-C63 A10-B13-C64 A10-B13-C65 A10-B13-C66 A10-B13-C67 A10-B13-C68A10-B13-C69 A10-B13-C70 A10-B13-C71 A10-B13-C72 A10-B13-C73 A10-B13-C74A10-B13-C75 A10-B13-C76 A10-B13-C77 A10-B13-C78 A10-B13-C79 A10-B13-C80A10-B13-C81 A10-B13-C82 A10-B13-C83 A10-B13-C84 A10-B13-C85 A10-B13-C86A10-B13-C87 A10-B13-C88 A10-B13-C89 A10-B13-C90 A10-B13-C91 A10-B13-C92A10-B13-C93 A10-B13-C94 A10-B13-C95 A10-B13-C96 A10-B13-C97 A10-B13-C98A10-B13-C99 A10-B13-C100 A10-B13-C101 A10-B13-C102 A10-B13-C103A10-B13-C104 A10-B13-C105 A10-B13-C106 A10-B13-C107 A10-B13-C108A10-B13-C109 A10-B13-C110 A10-B13-C111 A10-B13-C112 A10-B13-C113A10-B13-C114 A10-B13-C115 A10-B13-C116 A10-B13-C117 A10-B13-C118A10-B13-C119 A10-B13-C120 A10-B13-C121 A10-B13-C122 A10-B13-C123A10-B13-C124 A10-B13-C125 A10-B13-C126 A10-B13-C127 A10-B13-C128A10-B13-C129 A10-B13-C130 A10-B13-C131 A10-B13-C132 A10-B13-C133A10-B13-C134 A10-B13-C135 A10-B13-C136 A10-B13-C137 A10-B13-C138A10-B13-C139 A10-B13-C140 BLANK BLANK BLANK BLANK A11-B1-C1 A11-B1-C2A11-B1-C3 A11-B1-C4 A11-B1-C5 A11-B1-C6 A11-B1-C7 A11-B1-C8 A11-B1-C9A11-B1-C10 A11-B1-C11 A11-B1-C12 A11-B1-C13 A11-B1-C14 A11-B1-C15A11-B1-C16 A11-B1-C17 A11-B1-C18 A11-B1-C19 A11-B1-C20 A11-B1-C21A11-B1-C22 A11-B1-C23 A11-B1-C24 A11-B1-C25 A11-B1-C26 A11-B1-C27A11-B1-C28 A11-B1-C29 A11-B1-C30 A11-B1-C31 A11-B1-C32 A11-B1-C33A11-B1-C34 A11-B1-C35 A11-B1-C36 A11-B1-C37 A11-B1-C38 A11-B1-C39A11-B1-C40 A11-B1-C41 A11-B1-C42 A11-B1-C43 A11-B1-C44 A11-B1-C45A11-B1-C46 A11-B1-C47 A11-B1-C48 A11-B1-C49 A11-B1-C50 A11-B1-C51A11-B1-C52 A11-B1-C53 A11-B1-C54 A11-B1-C55 A11-B1-C56 A11-B1-C57A11-B1-C58 A11-B1-C59 A11-B1-C60 A11-B1-C61 A11-B1-C62 A11-B1-C63A11-B1-C64 A11-B1-C65 A11-B1-C66 A11-B1-C67 A11-B1-C68 A11-B1-C69A11-B1-C70 A11-B1-C71 A11-B1-C72 A11-B1-C73 A11-B1-C74 A11-B1-C75A11-B1-C76 A11-B1-C77 A11-B1-C78 A11-B1-C79 A11-B1-C80 A11-B1-C81A11-B1-C82 A11-B1-C83 A11-B1-C84 A11-B1-C85 A11-B1-C86 A11-B1-C87A11-B1-C88 A11-B1-C89 A11-B1-C90 A11-B1-C91 A11-B1-C92 A11-B1-C93A11-B1-C94 A11-B1-C95 A11-B1-C96 A11-B1-C97 A11-B1-C98 A11-B1-C99A11-B1-C100 A11-B1-C101 A11-B1-C102 A11-B1-C103 A11-B1-C104 A11-B1-C105A11-B1-C106 A11-B1-C107 A11-B1-C108 A11-B1-C109 A11-B1-C110 A11-B1-C111A11-B1-C112 A11-B1-C113 A11-B1-C114 A11-B1-C115 A11-B1-C116 A11-B1-C117A11-B1-C118 A11-B1-C119 A11-B1-C120 A11-B1-C121 A11-B1-C122 A11-B1-C123A11-B1-C124 A11-B1-C125 A11-B1-C126 A11-B1-C127 A11-B1-C128 A11-B1-C129A11-B1-C130 A11-B1-C131 A11-B1-C132 A11-B1-C133 A11-B1-C134 A11-B1-C135A11-B1-C136 A11-B1-C137 A11-B1-C138 A11-B1-C139 A11-B1-C140 BLANK BLANKBLANK BLANK A11-B2-C1 A11-B2-C2 A11-B2-C3 A11-B2-C4 A11-B2-C5 A11-B2-C6A11-B2-C7 A11-B2-C8 A11-B2-C9 A11-B2-C10 A11-B2-C11 A11-B2-C12A11-B2-C13 A11-B2-C14 A11-B2-C15 A11-B2-C16 A11-B2-C17 A11-B2-C18A11-B2-C19 A11-B2-C20 A11-B2-C21 A11-B2-C22 A11-B2-C23 A11-B2-C24A11-B2-C25 A11-B2-C26 A11-B2-C27 A11-B2-C28 A11-B2-C29 A11-B2-C30A11-B2-C31 A11-B2-C32 A11-B2-C33 A11-B2-C34 A11-B2-C35 A11-B2-C36A11-B2-C37 A11-B2-C38 A11-B2-C39 A11-B2-C40 A11-B2-C41 A11-B2-C42A11-B2-C43 A11-B2-C44 A11-B2-C45 A11-B2-C46 A11-B2-C47 A11-B2-C48A11-B2-C49 A11-B2-C50 A11-B2-C51 A11-B2-C52 A11-B2-C53 A11-B2-C54A11-B2-C55 A11-B2-C56 A11-B2-C57 A11-B2-C58 A11-B2-C59 A11-B2-C60A11-B2-C61 A11-B2-C62 A11-B2-C63 A11-B2-C64 A11-B2-C65 A11-B2-C66A11-B2-C67 A11-B2-C68 A11-B2-C69 A11-B2-C70 A11-B2-C71 A11-B2-C72A11-B2-C73 A11-B2-C74 A11-B2-C75 A11-B2-C76 A11-B2-C77 A11-B2-C78A11-B2-C79 A11-B2-C80 A11-B2-C81 A11-B2-C82 A11-B2-C83 A11-B2-C84A11-B2-C85 A11-B2-C86 A11-B2-C87 A11-B2-C88 A11-B2-C89 A11-B2-C90A11-B2-C91 A11-B2-C92 A11-B2-C93 A11-B2-C94 A11-B2-C95 A11-B2-C96A11-B2-C97 A11-B2-C98 A11-B2-C99 A11-B2-C100 A11-B2-C101 A11-B2-C102A11-B2-C103 A11-B2-C104 A11-B2-C105 A11-B2-C106 A11-B2-C107 A11-B2-C108A11-B2-C109 A11-B2-C110 A11-B2-C111 A11-B2-C112 A11-B2-C113 A11-B2-C114A11-B2-C115 A11-B2-C116 A11-B2-C117 A11-B2-C118 A11-B2-C119 A11-B2-C120A11-B2-C121 A11-B2-C122 A11-B2-C123 A11-B2-C124 A11-B2-C125 A11-B2-C126A11-B2-C127 A11-B2-C128 A11-B2-C129 A11-B2-C130 A11-B2-C131 A11-B2-C132A11-B2-C133 A11-B2-C134 A11-B2-C135 A11-B2-C136 A11-B2-C137 A11-B2-C138A11-B2-C139 A11-B2-C140 BLANK BLANK BLANK BLANK A11-B3-C1 A11-B3-C2A11-B3-C3 A11-B3-C4 A11-B3-C5 A11-B3-C6 A11-B3-C7 A11-B3-C8 A11-B3-C9A11-B3-C10 A11-B3-C11 A11-B3-C12 A11-B3-C13 A11-B3-C14 A11-B3-C15A11-B3-C16 A11-B3-C17 A11-B3-C18 A11-B3-C19 A11-B3-C20 A11-B3-C21A11-B3-C22 A11-B3-C23 A11-B3-C24 A11-B3-C25 A11-B3-C26 A11-B3-C27A11-B3-C28 A11-B3-C29 A11-B3-C30 A11-B3-C31 A11-B3-C32 A11-B3-C33A11-B3-C34 A11-B3-C35 A11-B3-C36 A11-B3-C37 A11-B3-C38 A11-B3-C39A11-B3-C40 A11-B3-C41 A11-B3-C42 A11-B3-C43 A11-B3-C44 A11-B3-C45A11-B3-C46 A11-B3-C47 A11-B3-C48 A11-B3-C49 A11-B3-C50 A11-B3-C51A11-B3-C52 A11-B3-C53 A11-B3-C54 A11-B3-C55 A11-B3-C56 A11-B3-C57A11-B3-C58 A11-B3-C59 A11-B3-C60 A11-B3-C61 A11-B3-C62 A11-B3-C63A11-B3-C64 A11-B3-C65 A11-B3-C66 A11-B3-C67 A11-B3-C68 A11-B3-C69A11-B3-C70 A11-B3-C71 A11-B3-C72 A11-B3-C73 A11-B3-C74 A11-B3-C75A11-B3-C76 A11-B3-C77 A11-B3-C78 A11-B3-C79 A11-B3-C80 A11-B3-C81A11-B3-C82 A11-B3-C83 A11-B3-C84 A11-B3-C85 A11-B3-C86 A11-B3-C87A11-B3-C88 A11-B3-C89 A11-B3-C90 A11-B3-C91 A11-B3-C92 A11-B3-C93A11-B3-C94 A11-B3-C95 A11-B3-C96 A11-B3-C97 A11-B3-C98 A11-B3-C99A11-B3-C100 A11-B3-C101 A11-B3-C102 A11-B3-C103 A11-B3-C104 A11-B3-C105A11-B3-C106 A11-B3-C107 A11-B3-C108 A11-B3-C109 A11-B3-C110 A11-B3-C111A11-B3-C112 A11-B3-C113 A11-B3-C114 A11-B3-C115 A11-B3-C116 A11-B3-C117A11-B3-C118 A11-B3-C119 A11-B3-C120 A11-B3-C121 A11-B3-C122 A11-B3-C123A11-B3-C124 A11-B3-C125 A11-B3-C126 A11-B3-C127 A11-B3-C128 A11-B3-C129A11-B3-C130 A11-B3-C131 A11-B3-C132 A11-B3-C133 A11-B3-C134 A11-B3-C135A11-B3-C136 A11-B3-C137 A11-B3-C138 A11-B3-C139 A11-B3-C140 BLANK BLANKBLANK BLANK A11-B4-C1 A11-B4-C2 A11-B4-C3 A11-B4-C4 A11-B4-C5 A11-B4-C6A11-B4-C7 A11-B4-C8 A11-B4-C9 A11-B4-C10 A11-B4-C11 A11-B4-C12A11-B4-C13 A11-B4-C14 A11-B4-C15 A11-B4-C16 A11-B4-C17 A11-B4-C18A11-B4-C19 A11-B4-C20 A11-B4-C21 A11-B4-C22 A11-B4-C23 A11-B4-C24A11-B4-C25 A11-B4-C26 A11-B4-C27 A11-B4-C28 A11-B4-C29 A11-B4-C30A11-B4-C31 A11-B4-C32 A11-B4-C33 A11-B4-C34 A11-B4-C35 A11-B4-C36A11-B4-C37 A11-B4-C38 A11-B4-C39 A11-B4-C40 A11-B4-C41 A11-B4-C42A11-B4-C43 A11-B4-C44 A11-B4-C45 A11-B4-C46 A11-B4-C47 A11-B4-C48A11-B4-C49 A11-B4-C50 A11-B4-C51 A11-B4-C52 A11-B4-C53 A11-B4-C54A11-B4-C55 A11-B4-C56 A11-B4-C57 A11-B4-C58 A11-B4-C59 A11-B4-C60A11-B4-C61 A11-B4-C62 A11-B4-C63 A11-B4-C64 A11-B4-C65 A11-B4-C66A11-B4-C67 A11-B4-C68 A11-B4-C69 A11-B4-C70 A11-B4-C71 A11-B4-C72A11-B4-C73 A11-B4-C74 A11-B4-C75 A11-B4-C76 A11-B4-C77 A11-B4-C78A11-B4-C79 A11-B4-C80 A11-B4-C81 A11-B4-C82 A11-B4-C83 A11-B4-C84A11-B4-C85 A11-B4-C86 A11-B4-C87 A11-B4-C88 A11-B4-C89 A11-B4-C90A11-B4-C91 A11-B4-C92 A11-B4-C93 A11-B4-C94 A11-B4-C95 A11-B4-C96A11-B4-C97 A11-B4-C98 A11-B4-C99 A11-B4-C100 A11-B4-C101 A11-B4-C102A11-B4-C103 A11-B4-C104 A11-B4-C105 A11-B4-C106 A11-B4-C107 A11-B4-C108A11-B4-C109 A11-B4-C110 A11-B4-C111 A11-B4-C112 A11-B4-C113 A11-B4-C114A11-B4-C115 A11-B4-C116 A11-B4-C117 A11-B4-C118 A11-B4-C119 A11-B4-C120A11-B4-C121 A11-B4-C122 A11-B4-C123 A11-B4-C124 A11-B4-C125 A11-B4-C126A11-B4-C127 A11-B4-C128 A11-B4-C129 A11-B4-C130 A11-B4-C131 A11-B4-C132A11-B4-C133 A11-B4-C134 A11-B4-C135 A11-B4-C136 A11-B4-C137 A11-B4-C138A11-B4-C139 A11-B4-C140 BLANK BLANK BLANK BLANK A11-B5-C1 A11-B5-C2A11-B5-C3 A11-B5-C4 A11-B5-C5 A11-B5-C6 A11-B5-C7 A11-B5-C8 A11-B5-C9A11-B5-C10 A11-B5-C11 A11-B5-C12 A11-B5-C13 A11-B5-C14 A11-B5-C15A11-B5-C16 A11-B5-C17 A11-B5-C18 A11-B5-C19 A11-B5-C20 A11-B5-C21A11-B5-C22 A11-B5-C23 A11-B5-C24 A11-B5-C25 A11-B5-C26 A11-B5-C27A11-B5-C28 A11-B5-C29 A11-B5-C30 A11-B5-C31 A11-B5-C32 A11-B5-C33A11-B5-C34 A11-B5-C35 A11-B5-C36 A11-B5-C37 A11-B5-C38 A11-B5-C39A11-B5-C40 A11-B5-C41 A11-B5-C42 A11-B5-C43 A11-B5-C44 A11-B5-C45A11-B5-C46 A11-B5-C47 A11-B5-C48 A11-B5-C49 A11-B5-C50 A11-B5-C51A11-B5-C52 A11-B5-C53 A11-B5-C54 A11-B5-C55 A11-B5-C56 A11-B5-C57A11-B5-C58 A11-B5-C59 A11-B5-C60 A11-B5-C61 A11-B5-C62 A11-B5-C63A11-B5-C64 A11-B5-C65 A11-B5-C66 A11-B5-C67 A11-B5-C68 A11-B5-C69A11-B5-C70 A11-B5-C71 A11-B5-C72 A11-B5-C73 A11-B5-C74 A11-B5-C75A11-B5-C76 A11-B5-C77 A11-B5-C78 A11-B5-C79 A11-B5-C80 A11-B5-C81A11-B5-C82 A11-B5-C83 A11-B5-C84 A11-B5-C85 A11-B5-C86 A11-B5-C87A11-B5-C88 A11-B5-C89 A11-B5-C90 A11-B5-C91 A11-B5-C92 A11-B5-C93A11-B5-C94 A11-B5-C95 A11-B5-C96 A11-B5-C97 A11-B5-C98 A11-B5-C99A11-B5-C100 A11-B5-C101 A11-B5-C102 A11-B5-C103 A11-B5-C104 A11-B5-C105A11-B5-C106 A11-B5-C107 A11-B5-C108 A11-B5-C109 A11-B5-C110 A11-B5-C111A11-B5-C112 A11-B5-C113 A11-B5-C114 A11-B5-C115 A11-B5-C116 A11-B5-C117A11-B5-C118 A11-B5-C119 A11-B5-C120 A11-B5-C121 A11-B5-C122 A11-B5-C123A11-B5-C124 A11-B5-C125 A11-B5-C126 A11-B5-C127 A11-B5-C128 A11-B5-C129A11-B5-C130 A11-B5-C131 A11-B5-C132 A11-B5-C133 A11-B5-C134 A11-B5-C135A11-B5-C136 A11-B5-C137 A11-B5-C138 A11-B5-C139 A11-B5-C140 BLANK BLANKBLANK BLANK A11-B6-C1 A11-B6-C2 A11-B6-C3 A11-B6-C4 A11-B6-C5 A11-B6-C6A11-B6-C7 A11-B6-C8 A11-B6-C9 A11-B6-C10 A11-B6-C11 A11-B6-C12A11-B6-C13 A11-B6-C14 A11-B6-C15 A11-B6-C16 A11-B6-C17 A11-B6-C18A11-B6-C19 A11-B6-C20 A11-B6-C21 A11-B6-C22 A11-B6-C23 A11-B6-C24A11-B6-C25 A11-B6-C26 A11-B6-C27 A11-B6-C28 A11-B6-C29 A11-B6-C30A11-B6-C31 A11-B6-C32 A11-B6-C33 A11-B6-C34 A11-B6-C35 A11-B6-C36A11-B6-C37 A11-B6-C38 A11-B6-C39 A11-B6-C40 A11-B6-C41 A11-B6-C42A11-B6-C43 A11-B6-C44 A11-B6-C45 A11-B6-C46 A11-B6-C47 A11-B6-C48A11-B6-C49 A11-B6-C50 A11-B6-C51 A11-B6-C52 A11-B6-C53 A11-B6-C54A11-B6-C55 A11-B6-C56 A11-B6-C57 A11-B6-C58 A11-B6-C59 A11-B6-C60A11-B6-C61 A11-B6-C62 A11-B6-C63 A11-B6-C64 A11-B6-C65 A11-B6-C66A11-B6-C67 A11-B6-C68 A11-B6-C69 A11-B6-C70 A11-B6-C71 A11-B6-C72A11-B6-C73 A11-B6-C74 A11-B6-C75 A11-B6-C76 A11-B6-C77 A11-B6-C78A11-B6-C79 A11-B6-C80 A11-B6-C81 A11-B6-C82 A11-B6-C83 A11-B6-C84A11-B6-C85 A11-B6-C86 A11-B6-C87 A11-B6-C88 A11-B6-C89 A11-B6-C90A11-B6-C91 A11-B6-C92 A11-B6-C93 A11-B6-C94 A11-B6-C95 A11-B6-C96A11-B6-C97 A11-B6-C98 A11-B6-C99 A11-B6-C100 A11-B6-C101 A11-B6-C102A11-B6-C103 A11-B6-C104 A11-B6-C105 A11-B6-C106 A11-B6-C107 A11-B6-C108A11-B6-C109 A11-B6-C110 A11-B6-C111 A11-B6-C112 A11-B6-C113 A11-B6-C114A11-B6-C115 A11-B6-C116 A11-B6-C117 A11-B6-C118 A11-B6-C119 A11-B6-C120A11-B6-C121 A11-B6-C122 A11-B6-C123 A11-B6-C124 A11-B6-C125 A11-B6-C126A11-B6-C127 A11-B6-C128 A11-B6-C129 A11-B6-C130 A11-B6-C131 A11-B6-C132A11-B6-C133 A11-B6-C134 A11-B6-C135 A11-B6-C136 A11-B6-C137 A11-B6-C138A11-B6-C139 A11-B6-C140 BLANK BLANK BLANK BLANK A11-B7-C1 A11-B7-C2A11-B7-C3 A11-B7-C4 A11-B7-C5 A11-B7-C6 A11-B7-C7 A11-B7-C8 A11-B7-C9A11-B7-C10 A11-B7-C11 A11-B7-C12 A11-B7-C13 A11-B7-C14 A11-B7-C15A11-B7-C16 A11-B7-C17 A11-B7-C18 A11-B7-C19 A11-B7-C20 A11-B7-C21A11-B7-C22 A11-B7-C23 A11-B7-C24 A11-B7-C25 A11-B7-C26 A11-B7-C27A11-B7-C28 A11-B7-C29 A11-B7-C30 A11-B7-C31 A11-B7-C32 A11-B7-C33A11-B7-C34 A11-B7-C35 A11-B7-C36 A11-B7-C37 A11-B7-C38 A11-B7-C39A11-B7-C40 A11-B7-C41 A11-B7-C42 A11-B7-C43 A11-B7-C44 A11-B7-C45A11-B7-C46 A11-B7-C47 A11-B7-C48 A11-B7-C49 A11-B7-C50 A11-B7-C51A11-B7-C52 A11-B7-C53 A11-B7-C54 A11-B7-C55 A11-B7-C56 A11-B7-C57A11-B7-C58 A11-B7-C59 A11-B7-C60 A11-B7-C61 A11-B7-C62 A11-B7-C63A11-B7-C64 A11-B7-C65 A11-B7-C66 A11-B7-C67 A11-B7-C68 A11-B7-C69A11-B7-C70 A11-B7-C71 A11-B7-C72 A11-B7-C73 A11-B7-C74 A11-B7-C75A11-B7-C76 A11-B7-C77 A11-B7-C78 A11-B7-C79 A11-B7-C80 A11-B7-C81A11-B7-C82 A11-B7-C83 A11-B7-C84 A11-B7-C85 A11-B7-C86 A11-B7-C87A11-B7-C88 A11-B7-C89 A11-B7-C90 A11-B7-C91 A11-B7-C92 A11-B7-C93A11-B7-C94 A11-B7-C95 A11-B7-C96 A11-B7-C97 A11-B7-C98 A11-B7-C99A11-B7-C100 A11-B7-C101 A11-B7-C102 A11-B7-C103 A11-B7-C104 A11-B7-C105A11-B7-C106 A11-B7-C107 A11-B7-C108 A11-B7-C109 A11-B7-C110 A11-B7-C111A11-B7-C112 A11-B7-C113 A11-B7-C114 A11-B7-C115 A11-B7-C116 A11-B7-C117A11-B7-C118 A11-B7-C119 A11-B7-C120 A11-B7-C121 A11-B7-C122 A11-B7-C123A11-B7-C124 A11-B7-C125 A11-B7-C126 A11-B7-C127 A11-B7-C128 A11-B7-C129A11-B7-C130 A11-B7-C131 A11-B7-C132 A11-B7-C133 A11-B7-C134 A11-B7-C135A11-B7-C136 A11-B7-C137 A11-B7-C138 A11-B7-C139 A11-B7-C140 BLANK BLANKBLANK BLANK A11-B8-C1 A11-B8-C2 A11-B8-C3 A11-B8-C4 A11-B8-C5 A11-B8-C6A11-B8-C7 A11-B8-C8 A11-B8-C9 A11-B8-C10 A11-B8-C11 A11-B8-C12A11-B8-C13 A11-B8-C14 A11-B8-C15 A11-B8-C16 A11-B8-C17 A11-B8-C18A11-B8-C19 A11-B8-C20 A11-B8-C21 A11-B8-C22 A11-B8-C23 A11-B8-C24A11-B8-C25 A11-B8-C26 A11-B8-C27 A11-B8-C28 A11-B8-C29 A11-B8-C30A11-B8-C31 A11-B8-C32 A11-B8-C33 A11-B8-C34 A11-B8-C35 A11-B8-C36A11-B8-C37 A11-B8-C38 A11-B8-C39 A11-B8-C40 A11-B8-C41 A11-B8-C42A11-B8-C43 A11-B8-C44 A11-B8-C45 A11-B8-C46 A11-B8-C47 A11-B8-C48A11-B8-C49 A11-B8-C50 A11-B8-C51 A11-B8-C52 A11-B8-C53 A11-B8-C54A11-B8-C55 A11-B8-C56 A11-B8-C57 A11-B8-C58 A11-B8-C59 A11-B8-C60A11-B8-C61 A11-B8-C62 A11-B8-C63 A11-B8-C64 A11-B8-C65 A11-B8-C66A11-B8-C67 A11-B8-C68 A11-B8-C69 A11-B8-C70 A11-B8-C71 A11-B8-C72A11-B8-C73 A11-B8-C74 A11-B8-C75 A11-B8-C76 A11-B8-C77 A11-B8-C78A11-B8-C79 A11-B8-C80 A11-B8-C81 A11-B8-C82 A11-B8-C83 A11-B8-C84A11-B8-C85 A11-B8-C86 A11-B8-C87 A11-B8-C88 A11-B8-C89 A11-B8-C90A11-B8-C91 A11-B8-C92 A11-B8-C93 A11-B8-C94 A11-B8-C95 A11-B8-C96A11-B8-C97 A11-B8-C98 A11-B8-C99 A11-B8-C100 A11-B8-C101 A11-B8-C102A11-B8-C103 A11-B8-C104 A11-B8-C105 A11-B8-C106 A11-B8-C107 A11-B8-C108A11-B8-C109 A11-B8-C110 A11-B8-C111 A11-B8-C112 A11-B8-C113 A11-B8-C114A11-B8-C115 A11-B8-C116 A11-B8-G117 A11-B8-C118 A11-B8-C119 A11-B8-C120A11-B8-C121 A11-B8-C122 A11-B8-C123 A11-B8-C124 A11-B8-C125 A11-B8-C126A11-B8-C127 A11-B8-C128 A11-B8-C129 A11-B8-C130 A11-B8-C131 A11-B8-C132A11-B8-C133 A11-B8-C134 A11-B8-C135 A11-B8-C136 A11-B8-C137 A11-B8-C138A11-B8-C139 A11-B8-C140 BLANK BLANK BLANK BLANK A11-B9-C1 A11-B9-C2A11-B9-C3 A11-B9-C4 A11-B9-C5 A11-B9-C6 A11-B9-C7 A11-B9-C8 A11-B9-C9A11-B9-C10 A11-B9-C11 A11-B9-C12 A11-B9-C13 A11-B9-C14 A11-B9-C15A11-B9-C16 A11-B9-C17 A11-B9-C18 A11-B9-C19 A11-B9-C20 A11-B9-C21A11-B9-C22 A11-B9-C23 A11-B9-C24 A11-B9-C25 A11-B9-C26 A11-B9-C27A11-B9-C28 A11-B9-C29 A11-B9-C30 A11-B9-C31 A11-B9-C32 A11-B9-C33A11-B9-C34 A11-B9-C35 A11-B9-C36 A11-B9-C37 A11-B9-C38 A11-B9-C39A11-B9-C40 A11-B9-C41 A11-B9-C42 A11-B9-C43 A11-B9-C44 A11-B9-C45A11-B9-C46 A11-B9-C47 A11-B9-C48 A11-B9-C49 A11-B9-C50 A11-B9-C51A11-B9-C52 A11-B9-C53 A11-B9-C54 A11-B9-C55 A11-B9-C56 A11-B9-C57A11-B9-C58 A11-B9-C59 A11-B9-C60 A11-B9-C61 A11-B9-C62 A11-B9-C63A11-B9-C64 A11-B9-C65 A11-B9-C66 A11-B9-C67 A11-B9-C68 A11-B9-C69A11-B9-C70 A11-B9-C71 A11-B9-C72 A11-B9-C73 A11-B9-C74 A11-B9-C75A11-B9-C76 A11-B9-C77 A11-B9-C78 A11-B9-C79 A11-B9-C80 A11-B9-C81A11-B9-C82 A11-B9-C83 A11-B9-C84 A11-B9-C85 A11-B9-C86 A11-B9-C87A11-B9-C88 A11-B9-C89 A11-B9-C90 A11-B9-C91 A11-B9-C92 A11-B9-C93A11-B9-C94 A11-B9-C95 A11-B9-C96 A11-B9-C97 A11-B9-C98 A11-B9-C99A11-B9-C100 A11-B9-C101 A11-B9-C102 A11-B9-C103 A11-B9-C104 A11-B9-C105A11-B9-C106 A11-B9-C107 A11-B9-C108 A11-B9-C109 A11-B9-C110 A11-B9-C111A11-B9-C112 A11-B9-C113 A11-B9-C114 A11-B9-C115 A11-B9-C116 A11-B9-C117A11-B9-C118 A11-B9-C119 A11-B9-C120 A11-B9-C121 A11-B9-C122 A11-B9-C123A11-B9-C124 A11-B9-C125 A11-B9-C126 A11-B9-C127 A11-B9-C128 A11-B9-C129A11-B9-C130 A11-B9-C131 A11-B9-C132 A11-B9-C133 A11-B9-C134 A11-B9-C135A11-B9-C136 A11-B9-C137 A11-B9-C138 A11-B9-C139 A11-B9-C140 BLANK BLANKBLANK BLANK A11-B10-C1 A11-B10-C2 A11-B10-C3 A11-B10-C4 A11-B10-C5A11-B10-C6 A11-B10-C7 A11-B10-C8 A11-B10-C9 A11-B10-C10 A11-B10-C11A11-B10-C12 A11-B10-C13 A11-B10-C14 A11-B10-C15 A11-B10-C16 A11-B10-C17A11-B10-C18 A11-B10-C19 A11-B10-C20 A11-B10-C21 A11-B10-C22 A11-B10-C23A11-B10-C24 A11-B10-C25 A11-B10-C26 A11-B10-C27 A11-B10-C28 A11-B10-C29A11-B10-C30 A11-B10-C31 A11-B10-C32 A11-B10-C33 A11-B10-C34 A11-B10-C35A11-B10-C36 A11-B10-C37 A11-B10-C38 A11-B10-C39 A11-B10-C40 A11-B10-C41A11-B10-C42 A11-B10-C43 A11-B10-C44 A11-B10-C45 A11-B10-C46 A11-B10-C47A11-B10-C48 A11-B10-C49 A11-B10-C50 A11-B10-C51 A11-B10-C52 A11-B10-C53A11-B10-C54 A11-B10-C55 A11-B10-C56 A11-B10-C57 A11-B10-C58 A11-B10-C59A11-B10-C60 A11-B10-C61 A11-B10-C62 A11-B10-C63 A11-B10-C64 A11-B10-C65A11-B10-C66 A11-B10-C67 A11-B10-C68 A11-B10-C69 A11-B10-C70 A11-B10-C71A11-B10-C72 A11-B10-C73 A11-B10-C74 A11-B10-C75 A11-B10-C76 A11-B10-C77A11-B10-C78 A11-B10-C79 A11-B10-C80 A11-B10-C81 A11-B10-C82 A11-B10-C83A11-B10-C84 A11-B10-C85 A11-B10-C86 A11-B10-C87 A11-B10-C88 A11-B10-C89A11-B10-C90 A11-B10-C91 A11-B10-C92 A11-B10-C93 A11-B10-C94 A11-B10-C95A11-B10-C96 A11-B10-C97 A11-B10-C98 A11-B10-C99 A11-B10-C100A11-B10-C101 A11-B10-C102 A11-B10-C103 A11-B10-C104 A11-B10-C105A11-B10-C106 A11-B10-C107 A11-B10-C108 A11-B10-C109 A11-B10-C110A11-B10-C111 A11-B10-C112 A11-B10-C113 A11-B10-C114 A11-B10-C115A11-B10-C116 A11-B10-C117 A11-B10-C118 A11-B10-C119 A11-B10-C120A11-B10-C121 A11-B10-C122 A11-B10-C123 A11-B10-C124 A11-B10-C125A11-B10-C126 A11-B10-C127 A11-B10-C128 A11-B10-C129 A11-B10-C130A11-B10-C131 A11-B10-C132 A11-B10-C133 A11-B10-C134 A11-B10-C135A11-B10-C136 A11-B10-C137 A11-B10-C138 A11-B10-C139 A11-B10-C140 BLANKBLANK BLANK BLANK A11-B11-C1 A11-B11-C2 A11-B11-C3 A11-B11-C4 A11-B11-C5A11-B11-C6 A11-B11-C7 A11-B11-C8 A11-B11-C9 A11-B11-C10 A11-B11-C11A11-B11-C12 A11-B11-C13 A11-B11-C14 A11-B11-C15 A11-B11-C16 A11-B11-C17A11-B11-C18 A11-B11-C19 A11-B11-C20 A11-B11-C21 A11-B11-C22 A11-B11-C23A11-B11-C24 A11-B11-C25 A11-B11-C26 A11-B11-C27 A11-B11-C28 A11-B11-C29A11-B11-C30 A11-B11-C31 A11-B11-C32 A11-B11-C33 A11-B11-C34 A11-B11-C35A11-B11-C36 A11-B11-C37 A11-B11-C38 A11-B11-C39 A11-B11-C40 A11-B11-C41A11-B11-C42 A11-B11-C43 A11-B11-C44 A11-B11-C45 A11-B11-C46 A11-B11-C47A11-B11-C48 A11-B11-C49 A11-B11-C50 A11-B11-C51 A11-B11-C52 A11-B11-C53A11-B11-C54 A11-B11-C55 A11-B11-C56 A11-B11-C57 A11-B11-C58 A11-B11-C59A11-B11-C60 A11-B11-C61 A11-B11-C62 A11-B11-C63 A11-B11-C64 A11-B11-C65A11-B11-C66 A11-B11-C67 A11-B11-C68 A11-B11-C69 A11-B11-C70 A11-B11-C71A11-B11-C72 A11-B11-C73 A11-B11-C74 A11-B11-C75 A11-B11-C76 A11-B11-C77A11-B11-C78 A11-B11-C79 A11-B11-C80 A11-B11-C81 A11-B11-C82 A11-B11-C83A11-B11-C84 A11-B11-C85 A11-B11-C86 A11-B11-C87 A11-B11-C88 A11-B11-C89A11-B11-C90 A11-B11-C91 A11-B11-C92 A11-B11-C93 A11-B11-C94 A11-B11-C95A11-B11-C96 A11-B11-C97 A11-B11-C98 A11-B11-C99 A11-B11-C100A11-B11-C101 A11-B11-C102 A11-B11-C103 A11-B11-C104 A11-B11-C105A11-B11-C106 A11-B11-C107 A11-B11-C108 A11-B11-C109 A11-B11-C110A11-B11-C111 A11-B11-C112 A11-B11-C113 A11-B11-C114 A11-B11-C115A11-B11-C116 A11-B11-C117 A11-B11-C118 A11-B11-C119 A11-B11-C120A11-B11-C121 A11-B11-C122 A11-B11-C123 A11-B11-C124 A11-B11-C125A11-B11-C126 A11-B11-C127 A11-B11-C128 A11-B11-C129 A11-B11-C130A11-B11-C131 A11-B11-C132 A11-B11-C133 A11-B11-C134 A11-B11-C135A11-B11-C136 A11-B11-C137 A11-B11-C138 A11-B11-C139 A11-B11-C140 BLANKBLANK BLANK BLANK A11-B12-C1 A11-B12-C2 A11-B12-C3 A11-B12-C4 A11-B12-C5A11-B12-C6 A11-B12-C7 A11-B12-C8 A11-B12-C9 A11-B12-C10 A11-B12-C11A11-B12-C12 A11-B12-C13 A11-B12-C14 A11-B12-C15 A11-B12-C16 A11-B12-C17A11-B12-C18 A11-B12-C19 A11-B12-C20 A11-B12-C21 A11-B12-C22 A11-B12-C23A11-B12-C24 A11-B12-C25 A11-B12-C26 A11-B12-C27 A11-B12-C28 A11-B12-C29A11-B12-C30 A11-B12-C31 A11-B12-C32 A11-B12-C33 A11-B12-C34 A11-B12-C35A11-B12-C36 A11-B12-C37 A11-B12-C38 A11-B12-C39 A11-B12-C40 A11-B12-C41A11-B12-C42 A11-B12-C43 A11-B12-C44 A11-B12-C45 A11-B12-C46 A11-B12-C47A11-B12-C48 A11-B12-C49 A11-B12-C50 A11-B12-C51 A11-B12-C52 A11-B12-C53A11-B12-C54 A11-B12-C55 A11-B12-C56 A11-B12-C57 A11-B12-C58 A11-B12-C59A11-B12-C60 A11-B12-C61 A11-B12-C62 A11-B12-C63 A11-B12-C64 A11-B12-C65A11-B12-C66 A11-B12-C67 A11-B12-C68 A11-B12-C69 A11-B12-C70 A11-B12-C71A11-B12-C72 A11-B12-C73 A11-B12-C74 A11-B12-C75 A11-B12-C76 A11-B12-C77A11-B12-C78 A11-B12-C79 A11-B12-C80 A11-B12-C81 A11-B12-C82 A11-B12-C83A11-B12-C84 A11-B12-C85 A11-B12-C86 A11-B12-C87 A11-B12-C88 A11-B12-C89A11-B12-C90 A11-B12-C91 A11-B12-C92 A11-B12-C93 A11-B12-C94 A11-B12-C95A11-B12-C96 A11-B12-C97 A11-B12-C98 A11-B12-C99 A11-B12-C100A11-B12-C101 A11-B12-C102 A11-B12-C103 A11-B12-C104 A11-B12-C105A11-B12-C106 A11-B12-C107 A11-B12-C108 A11-B12-C109 A11-B12-C110A11-B12-C111 A11-B12-C112 A11-B12-C113 A11-B12-C114 A11-B12-C115A11-B12-C116 A11-B12-C117 A11-B12-C118 A11-B12-C119 A11-B12-C120A11-B12-C121 A11-B12-C122 A11-B12-C123 A11-B12-C124 A11-B12-C125A11-B12-C126 A11-B12-C127 A11-B12-C128 A11-B12-C129 A11-B12-C130A11-B12-C131 A11-B12-C132 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A11-B13-C75 A11-B13-C76 A11-B13-C77A11-B13-C78 A11-B13-C79 A11-B13-C80 A11-B13-C81 A11-B13-C82 A11-B13-C83A11-B13-C84 A11-B13-C85 A11-B13-C86 A11-B13-C87 A11-B13-C88 A11-B13-C89A11-B13-C90 A11-B13-C91 A11-B13-C92 A11-B13-C93 A11-B13-C94 A11-B13-C95A11-B13-C96 A11-B13-C97 A11-B13-C98 A11-B13-C99 A11-B13-C100A11-B13-C101 A11-B13-C102 A11-B13-C103 A11-B13-C104 A11-B13-C105A11-B13-C106 A11-B13-C107 A11-B13-C108 A11-B13-C109 A11-B13-C110A11-B13-C111 A11-B13-C112 A11-B13-C113 A11-B13-C114 A11-B13-C115A11-B13-C116 A11-B13-C117 A11-B13-C118 A11-B13-C119 A11-B13-C120A11-B13-C121 A11-B13-C122 A11-B13-C123 A11-B13-C124 A11-B13-C125A11-B13-C126 A11-B13-C127 A11-B13-C128 A11-B13-C129 A11-B13-C130A11-B13-C131 A11-B13-C132 A11-B13-C133 A11-B13-C134 A11-B13-C135A11-B13-C136 A11-B13-C137 A11-B13-C138 A11-B13-C139 A11-B13-C140 BLANKBLANK BLANK BLANK A12-B1-C1 A12-B1-C2 A12-B1-C3 A12-B1-C4 A12-B1-C5A12-B1-C6 A12-B1-C7 A12-B1-C8 A12-B1-C9 A12-B1-C10 A12-B1-C11 A12-B1-C12A12-B1-C13 A12-B1-C14 A12-B1-C15 A12-B1-C16 A12-B1-C17 A12-B1-C18A12-B1-C19 A12-B1-C20 A12-B1-C21 A12-B1-C22 A12-B1-C23 A12-B1-C24A12-B1-C25 A12-B1-C26 A12-B1-C27 A12-B1-C28 A12-B1-C29 A12-B1-C30A12-B1-C31 A12-B1-C32 A12-B1-C33 A12-B1-C34 A12-B1-C35 A12-B1-C36A12-B1-C37 A12-B1-C38 A12-B1-C39 A12-B1-C40 A12-B1-C41 A12-B1-C42A12-B1-C43 A12-B1-C44 A12-B1-C45 A12-B1-C46 A12-B1-C47 A12-B1-C48A12-B1-C49 A12-B1-C50 A12-B1-C51 A12-B1-C52 A12-B1-C53 A12-B1-C54A12-B1-C55 A12-B1-C56 A12-B1-C57 A12-B1-C58 A12-B1-C59 A12-B1-C60A12-B1-C61 A12-B1-C62 A12-B1-C63 A12-B1-C64 A12-B1-C65 A12-B1-C66A12-B1-C67 A12-B1-C68 A12-B1-C69 A12-B1-C70 A12-B1-C71 A12-B1-C72A12-B1-C73 A12-B1-C74 A12-B1-C75 A12-B1-C76 A12-B1-C77 A12-B1-C78A12-B1-C79 A12-B1-C80 A12-B1-C81 A12-B1-C82 A12-B1-C83 A12-B1-C84A12-B1-C85 A12-B1-C86 A12-B1-C87 A12-B1-C88 A12-B1-C89 A12-B1-C90A12-B1-C91 A12-B1-C92 A12-B1-C93 A12-B1-C94 A12-B1-C95 A12-B1-C96A12-B1-C97 A12-B1-C98 A12-B1-C99 A12-B1-C100 A12-B1-C101 A12-B1-C102A12-B1-C103 A12-B1-C104 A12-B1-C105 A12-B1-C106 A12-B1-C107 A12-B1-C108A12-B1-C109 A12-B1-C110 A12-B1-C111 A12-B1-C112 A12-B1-C113 A12-B1-C114A12-B1-C115 A12-B1-C116 A12-B1-C117 A12-B1-C118 A12-B1-C119 A12-B1-C120A12-B1-C121 A12-B1-C122 A12-B1-C123 A12-B1-C124 A12-B1-C125 A12-B1-C126A12-B1-C127 A12-B1-C128 A12-B1-C129 A12-B1-C130 A12-B1-C131 A12-B1-C132A12-B1-C133 A12-B1-C134 A12-B1-C135 A12-B1-C136 A12-B1-C137 A12-B1-C138A12-B1-C139 A12-B1-C140 BLANK BLANK BLANK BLANK A12-B2-C1 A12-B2-C2A12-B2-C3 A12-B2-C4 A12-B2-C5 A12-B2-C6 A12-B2-C7 A12-B2-C8 A12-B2-C9A12-B2-C10 A12-B2-C11 A12-B2-C12 A12-B2-C13 A12-B2-C14 A12-B2-C15A12-B2-C16 A12-B2-C17 A12-B2-C18 A12-B2-C19 A12-B2-C20 A12-B2-C21A12-B2-C22 A12-B2-C23 A12-B2-C24 A12-B2-C25 A12-B2-C26 A12-B2-C27A12-B2-C28 A12-B2-C29 A12-B2-C30 A12-B2-C31 A12-B2-C32 A12-B2-C33A12-B2-C34 A12-B2-C35 A12-B2-C36 A12-B2-C37 A12-B2-C38 A12-B2-C39A12-B2-C40 A12-B2-C41 A12-B2-C42 A12-B2-C43 A12-B2-C44 A12-B2-C45A12-B2-C46 A12-B2-C47 A12-B2-C48 A12-B2-C49 A12-B2-C50 A12-B2-C51A12-B2-C52 A12-B2-C53 A12-B2-C54 A12-B2-C55 A12-B2-C56 A12-B2-C57A12-B2-C58 A12-B2-C59 A12-B2-C60 A12-B2-C61 A12-B2-C62 A12-B2-C63A12-B2-C64 A12-B2-C65 A12-B2-C66 A12-B2-C67 A12-B2-C68 A12-B2-C69A12-B2-C70 A12-B2-C71 A12-B2-C72 A12-B2-C73 A12-B2-C74 A12-B2-C75A12-B2-C76 A12-B2-C77 A12-B2-C78 A12-B2-C79 A12-B2-C80 A12-B2-C81A12-B2-C82 A12-B2-C83 A12-B2-C84 A12-B2-C85 A12-B2-C86 A12-B2-C87A12-B2-C88 A12-B2-C89 A12-B2-C90 A12-B2-C91 A12-B2-C92 A12-B2-C93A12-B2-C94 A12-B2-C95 A12-B2-C96 A12-B2-C97 A12-B2-C98 A12-B2-C99A12-B2-C100 A12-B2-C101 A12-B2-C102 A12-B2-C103 A12-B2-C104 A12-B2-C105A12-B2-C106 A12-B2-C107 A12-B2-C108 A12-B2-C109 A12-B2-C110 A12-B2-C111A12-B2-C112 A12-B2-C113 A12-B2-C114 A12-B2-C115 A12-B2-C116 A12-B2-C117A12-B2-C118 A12-B2-C119 A12-B2-C120 A12-B2-C121 A12-B2-C122 A12-B2-C123A12-B2-C124 A12-B2-C125 A12-B2-C126 A12-B2-C127 A12-B2-C128 A12-B2-C129A12-B2-C130 A12-B2-C131 A12-B2-C132 A12-B2-C133 A12-B2-C134 A12-B2-C135A12-B2-C136 A12-B2-C137 A12-B2-C138 A12-B2-C139 A12-B2-C140 BLANK BLANKBLANK BLANK A12-B3-C1 A12-B3-C2 A12-B3-C3 A12-B3-C4 A12-B3-C5 A12-B3-C6A12-B3-C7 A12-B3-C8 A12-B3-C9 A12-B3-C10 A12-B3-C11 A12-B3-C12A12-B3-C13 A12-B3-C14 A12-B3-C15 A12-B3-C16 A12-B3-C17 A12-B3-C18A12-B3-C19 A12-B3-C20 A12-B3-C21 A12-B3-C22 A12-B3-C23 A12-B3-C24A12-B3-C25 A12-B3-C26 A12-B3-C27 A12-B3-C28 A12-B3-C29 A12-B3-C30A12-B3-C31 A12-B3-C32 A12-B3-C33 A12-B3-C34 A12-B3-C35 A12-B3-C36A12-B3-C37 A12-B3-C38 A12-B3-C39 A12-B3-C40 A12-B3-C41 A12-B3-C42A12-B3-C43 A12-B3-C44 A12-B3-C45 A12-B3-C46 A12-B3-C47 A12-B3-C48A12-B3-C49 A12-B3-C50 A12-B3-C51 A12-B3-C52 A12-B3-C53 A12-B3-C54A12-B3-C55 A12-B3-C56 A12-B3-C57 A12-B3-C58 A12-B3-C59 A12-B3-C60A12-B3-C61 A12-B3-C62 A12-B3-C63 A12-B3-C64 A12-B3-C65 A12-B3-C66A12-B3-C67 A12-B3-C68 A12-B3-C69 A12-B3-C70 A12-B3-C71 A12-B3-C72A12-B3-C73 A12-B3-C74 A12-B3-C75 A12-B3-C76 A12-B3-C77 A12-B3-C78A12-B3-C79 A12-B3-C80 A12-B3-C81 A12-B3-C82 A12-B3-C83 A12-B3-C84A12-B3-C85 A12-B3-C86 A12-B3-C87 A12-B3-C88 A12-B3-C89 A12-B3-C90A12-B3-C91 A12-B3-C92 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A12-B9-C48A12-B9-C49 A12-B9-C50 A12-B9-C51 A12-B9-C52 A12-B9-C53 A12-B9-C54A12-B9-C55 A12-B9-C56 A12-B9-C57 A12-B9-C58 A12-B9-C59 A12-B9-C60A12-B9-C61 A12-B9-C62 A12-B9-C63 A12-B9-C64 A12-B9-C65 A12-B9-C66A12-B9-C67 A12-B9-C68 A12-B9-C69 A12-B9-C70 A12-B9-C71 A12-B9-C72A12-B9-C73 A12-B9-C74 A12-B9-C75 A12-B9-C76 A12-B9-C77 A12-B9-C78A12-B9-C79 A12-B9-C80 A12-B9-C81 A12-B9-C82 A12-B9-C83 A12-B9-C84A12-B9-C85 A12-B9-C86 A12-B9-C87 A12-B9-C88 A12-B9-C89 A12-B9-C90A12-B9-C91 A12-B9-C92 A12-B9-C93 A12-B9-C94 A12-B9-C95 A12-B9-C96A12-B9-C97 A12-B9-C98 A12-B9-C99 A12-B9-C100 A12-B9-C101 A12-B9-C102A12-B9-C103 A12-B9-C104 A12-B9-C105 A12-B9-C106 A12-B9-C107 A12-B9-C108A12-B9-C109 A12-B9-C110 A12-B9-C111 A12-B9-C112 A12-B9-C113 A12-B9-C114A12-B9-C115 A12-B9-C116 A12-B9-C117 A12-B9-C118 A12-B9-C119 A12-B9-C120A12-B9-C121 A12-B9-C122 A12-B9-C123 A12-B9-C124 A12-B9-C125 A12-B9-C126A12-B9-C127 A12-B9-C128 A12-B9-C129 A12-B9-C130 A12-B9-C131 A12-B9-C132A12-B9-C133 A12-B9-C134 A12-B9-C135 A12-B9-C136 A12-B9-C137 A12-B9-C138A12-B9-C139 A12-B9-C140 BLANK BLANK BLANK BLALK A12-B10-C1 A12-B10-C2A12-B10-C3 A12-B10-C4 A12-B10-C5 A12-B10-C6 A12-B10-C7 A12-B10-C8A12-B10-C9 A12-B10-C10 A12-B10-C11 A12-B10-C12 A12-B10-C13 A12-B10-C14A12-B10-C15 A12-B10-C16 A12-B10-C17 A12-B10-C18 A12-B10-C19 A12-B10-C20A12-B10-C21 A12-B10-C22 A12-B10-C23 A12-B10-C24 A12-B10-C25 A12-B10-C26A12-B10-C27 A12-B10-C28 A12-B10-C29 A12-B10-C30 A12-B10-C31 A12-B10-C32A12-B10-C33 A12-B10-C34 A12-B10-C35 A12-B10-C36 A12-B10-C37 A12-B10-C38A12-B10-C39 A12-B10-C40 A12-B10-C41 A12-B10-C42 A12-B10-C43 A12-B10-C44A12-B10-C45 A12-B10-C46 A12-B10-C47 A12-B10-C48 A12-B10-C49 A12-B10-C50A12-B10-C51 A12-B10-C52 A12-B10-C53 A12-B10-C54 A12-B10-C55 A12-B10-C56A12-B10-C57 A12-B10-C58 A12-B10-C59 A12-B10-C60 A12-B10-C61 A12-B10-C62A12-B10-C63 A12-B10-C64 A12-B10-C65 A12-B10-C66 A12-B10-C67 A12-B10-C68A12-B10-C69 A12-B10-C70 A12-B10-C71 A12-B10-C72 A12-B10-C73 A12-B10-C74A12-B10-C75 A12-B10-C76 A12-B10-C77 A12-B10-C78 A12-B10-C79 A12-B10-C80A12-B10-C81 A12-B10-C82 A12-B10-C83 A12-B10-C84 A12-B10-C85 A12-B10-C86A12-B10-C87 A12-B10-C88 A12-B10-C89 A12-B10-C90 A12-B10-C91 A12-B10-C92A12-B10-C93 A12-B10-C94 A12-B10-C95 A12-B10-C96 A12-B10-C97 A12-B10-C98A12-B10-C99 A12-B10-C100 A12-B10-C101 A12-B10-C102 A12-B10-C103A12-B10-C104 A12-B10-C105 A12-B10-C106 A12-B10-C107 A12-B10-C108A12-B10-C109 A12-B10-C110 A12-B10-C111 A12-B10-C112 A12-B10-C113A12-B10-C114 A12-B10-C115 A12-B10-C116 A12-B10-C117 A12-B10-C118A12-B10-C119 A12-B10-C120 A12-B10-C121 A12-B10-C122 A12-B10-C123A12-B10-C124 A12-B10-C125 A12-B10-C126 A12-B10-C127 A12-B10-C128A12-B10-C129 A12-B10-C130 A12-B10-C131 A12-B10-C132 A12-B10-C133A12-B10-C134 A12-B10-C135 A12-B10-C136 A12-B10-C137 A12-B10-C138A12-B10-C139 A12-B10-C140 BLANK BLANK BLANK BLANK A12-B11-C1 A12-B11-C2A12-B11-C3 A12-B11-C4 A12-B11-C5 A12-B11-C6 A12-B11-C7 A12-B11-C8A12-B11-C9 A12-B11-C10 A12-B11-C11 A12-B11-C12 A12-B11-C13 A12-B11-C14A12-B11-C15 A12-B11-C16 A12-B11-C17 A12-B11-C18 A12-B11-C19 A12-B11-C20A12-B11-C21 A12-B11-C22 A12-B11-C23 A12-B11-C24 A12-B11-C25 A12-B11-C26A12-B11-C27 A12-B11-C28 A12-B11-C29 A12-B11-C30 A12-B11-C31 A12-B11-C32A12-B11-C33 A12-B11-C34 A12-B11-C35 A12-B11-C36 A12-B11-C37 A12-B11-C38A12-B11-C39 A12-B11-C40 A12-B11-C41 A12-B11-C42 A12-B11-C43 A12-B11-C44A12-B11-C45 A12-B11-C46 A12-B11-C47 A12-B11-C48 A12-B11-C49 A12-B11-C50A12-B11-C51 A12-B11-C52 A12-B11-C53 A12-B11-C54 A12-B11-C55 A12-B11-C56A12-B11-C57 A12-B11-C58 A12-B11-C59 A12-B11-C60 A12-B11-C61 A12-B11-C62A12-B11-C63 A12-B11-C64 A12-B11-C65 A12-B11-C66 A12-B11-C67 A12-B11-C68A12-B11-C69 A12-B11-C70 A12-B11-C71 A12-B11-C72 A12-B11-C73 A12-B11-C74A12-B11-C75 A12-B11-C76 A12-B11-C77 A12-B11-C78 A12-B11-C79 A12-B11-C80A12-B11-C81 A12-B11-C82 A12-B11-C83 A12-B11-C84 A12-B11-C85 A12-B11-C86A12-B11-C87 A12-B11-C88 A12-B11-C89 A12-B11-C90 A12-B11-C91 A12-B11-C92A12-B11-C93 A12-B11-C94 A12-B11-C95 A12-B11-C96 A12-B11-C97 A12-B11-C98A12-B11-C99 A12-B11-C100 A12-B11-C101 A12-B11-C102 A12-B11-C103A12-B11-C104 A12-B11-C105 A12-B11-C106 A12-B11-C107 A12-B11-C108A12-B11-C109 A12-B11-C110 A12-B11-C111 A12-B11-C112 A12-B11-C113A12-B11-C114 A12-B11-C115 A12-B11-C116 A12-B11-C117 A12-B11-C118A12-B11-C119 A12-B11-C120 A12-B11-C121 A12-B11-C122 A12-B11-C123A12-B11-C124 A12-B11-C125 A12-B11-C126 A12-B11-C127 A12-B11-C128A12-B11-C129 A12-B11-C130 A12-B11-C131 A12-B11-C132 A12-B11-C133A12-B11-C134 A12-B11-C135 A12-B11-C136 A12-B11-C137 A12-B11-C138A12-B11-C139 A12-B11-C140 BLANK BLANK BLANK BLANK A12-B12-C1 A12-B12-C2A12-B12-C3 A12-B12-C4 A12-B12-C5 A12-B12-C6 A12-B12-C7 A12-B12-C8A12-B12-C9 A12-B12-C10 A12-B12-C11 A12-B12-C12 A12-B12-C13 A12-B12-C14A12-B12-C15 A12-B12-C16 A12-B12-C17 A12-B12-C18 A12-B12-C19 A12-B12-C20A12-B12-C21 A12-B12-C22 A12-B12-C23 A12-B12-C24 A12-B12-C25 A12-B12-C26A12-B12-C27 A12-B12-C28 A12-B12-C29 A12-B12-C30 A12-B12-C31 A12-B12-C32A12-B12-C33 A12-B12-C34 A12-B12-C35 A12-B12-C36 A12-B12-C37 A12-B12-C38A12-B12-C39 A12-B12-C40 A12-B12-C41 A12-B12-C42 A12-B12-C43 A12-B12-C44A12-B12-C45 A12-B12-C46 A12-B12-C47 A12-B12-C48 A12-B12-C49 A12-B12-C50A12-B12-C51 A12-B12-C52 A12-B12-C53 A12-B12-C54 A12-B12-C55 A12-B12-C56A12-B12-C57 A12-B12-C58 A12-B12-C59 A12-B12-C60 A12-B12-C61 A12-B12-C62A12-B12-C63 A12-B12-C64 A12-B12-C65 A12-B12-C66 A12-B12-C67 A12-B12-C68A12-B12-C69 A12-B12-C70 A12-B12-C71 A12-B12-C72 A12-B12-C73 A12-B12-C74A12-B12-C75 A12-B12-C76 A12-B12-C77 A12-B12-C78 A12-B12-C79 A12-B12-C80A12-B12-C81 A12-B12-C82 A12-B12-C83 A12-B12-C84 A12-B12-C85 A12-B12-C86A12-B12-C87 A12-B12-C88 A12-B12-C89 A12-B12-C90 A12-B12-C91 A12-B12-C92A12-B12-C93 A12-B12-C94 A12-B12-C95 A12-B12-C96 A12-B12-C97 A12-B12-C98A12-B12-C99 A12-B12-C100 A12-B12-C101 A12-B12-C102 A12-B12-C103A12-B12-C104 A12-B12-C105 A12-B12-C106 A12-B12-C107 A12-B12-C108A12-B12-C109 A12-B12-C110 A12-B12-C111 A12-B12-C112 A12-B12-C113A12-B12-C114 A12-B12-C115 A12-B12-C116 A12-B12-C117 A12-B12-C118A12-B12-C119 A12-B12-C120 A12-B12-C121 A12-B12-C122 A12-B12-C123A12-B12-C124 A12-B12-C125 A12-B12-C126 A12-B12-C127 A12-B12-C128A12-B12-C129 A12-B12-C130 A12-B12-C131 A12-B12-C132 A12-B12-C133A12-B12-C134 A12-B12-C135 A12-B12-C136 A12-B12-C137 A12-B12-C138A12-B12-C139 A12-B12-C140 BLANK BLANK BLANK BLANK A12-B13-C1 A12-B13-C2A12-B13-C3 A12-B13-C4 A12-B13-C5 A12-B13-C6 A12-B13-C7 A12-B13-C8A12-B13-C9 A12-B13-C10 A12-B13-C11 A12-B13-C12 A12-B13-C13 A12-B13-C14A12-B13-C15 A12-B13-C16 A12-B13-C17 A12-B13-C18 A12-B13-C19 A12-B13-C20A12-B13-C21 A12-B13-C22 A12-B13-C23 A12-B13-C24 A12-B13-C25 A12-B13-C26A12-B13-C27 A12-B13-C28 A12-B13-C29 A12-B13-C30 A12-B13-C31 A12-B13-C32A12-B13-C33 A12-B13-C34 A12-B13-C35 A12-B13-C36 A12-B13-C37 A12-B13-C38A12-B13-C39 A12-B13-C40 A12-B13-C41 A12-B13-C42 A12-B13-C43 A12-B13-C44A12-B13-C45 A12-B13-C46 A12-B13-C47 A12-B13-C48 A12-B13-C49 A12-B13-C50A12-B13-C51 A12-B13-C52 A12-B13-C53 A12-B13-C54 A12-B13-C55 A12-B13-C56A12-B13-C57 A12-B13-C58 A12-B13-C59 A12-B13-C60 A12-B13-C61 A12-B13-C62A12-B13-C63 A12-B13-C64 A12-B13-C65 A12-B13-C66 A12-B13-C67 A12-B13-C68A12-B13-C69 A12-B13-C70 A12-B13-C71 A12-B13-C72 A12-B13-C73 A12-B13-C74A12-B13-C75 A12-B13-C76 A12-B13-C77 A12-B13-C78 A12-B13-C79 A12-B13-C80A12-B13-C81 A12-B13-C82 A12-B13-C83 A12-B13-C84 A12-B13-C85 A12-B13-C86A12-B13-C87 A12-B13-C88 A12-B13-C89 A12-B13-C90 A12-B13-C91 A12-B13-C92A12-B13-C93 A12-B13-C94 A12-B13-C95 A12-B13-C96 A12-B13-C97 A12-B13-C98A12-B13-C99 A12-B13-C100 A12-B13-C101 A12-B13-C102 A12-B13-C103A12-B13-C104 A12-B13-C105 A12-B13-C106 A12-B13-C107 A12-B13-C108A12-B13-C109 A12-B13-C110 A12-B13-C111 A12-B13-C112 A12-B13-C113A12-B13-C114 A12-B13-C115 A12-B13-C116 A12-B13-C117 A12-B13-C118A12-B13-C119 A12-B13-C120 A12-B13-C121 A12-B13-C122 A12-B13-C123A12-B13-C124 A12-B13-C125 A12-B13-C126 A12-B13-C127 A12-B13-C128A12-B13-C129 A12-B13-C130 A12-B13-C131 A12-B13-C132 A12-B13-C133A12-B13-C134 A12-B13-C135 A12-B13-C136 A12-B13-C137 A12-B13-C138A12-B13-C139 A12-B13-C140 BLANK BLANK BLANK BLANK.

Thus, for example, in the above list the compound denoted as A1-B1-C1 isthe product of the combination of group A1 in Table 1 and B1 in Table 2and C1 in Table 3, namely

Preferred compounds of the invention are selected from:

-   -   3-[1-(5-phenylethynyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamine;    -   3-[1-(3-phenylethyl-benzoyl)-piperidin-4-yl]-benzylamine;    -   3-{1-[3-(4-hydroxyphenyl)ethyl-benzoyl]-piperidin-4-yl}-benzylamine;    -   3-{1-[3-(6-amino-pyridin-3-yl)ethyl-benzoyl]-piperidin-4-yl}-benzylamine;    -   3-[1-(5-phenylethyl-thiophene-2-carbonyl)-piperidin-4-yl]-benzylamine;    -   4-fluoro-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamine;    -   4-methyl-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamine;    -   3-[1-(indole-6-carbonyl)-piperidin-4-yl]-benzylamine;    -   4-(3-aminomethyl-phenyl)-1-(5-phenethyl-pyridine-3-carbonyl)-piperidine-4-carbonitrile        [4-(3-aminomethylphenyl)piperidin-1-yl]-(3,4-dichlorophenyl)methanone;    -   1-{1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-3-methylsulfanyl-6,7-dihydro-5H-benzo[c]thiophen-4-one        trifluoroacetate;    -   1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(3-methylsulfanyl-6,7-dihydro-benzo[c]thiophen-1-yl)-methanone        trifluoroacetate;    -   1-{1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-3-ethylsulfanyl-6,6-dimethyl-6,7-dihydro-5H-benzo[c]thiophen-4-one        trifluoroacetate;    -   1-{1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-3-propylsulfanyl-6,7-dihydro-5H-benzo[c]thiophen-4-one        trifluoroacetate;    -   1-{1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-3-isopropylsulfanyl-6,7-dihydro-5H-benzo[c]thiophen-4-one        trifluoroacetate;    -   1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-benzo[b]thiophen-2-yl-methanone-trifluoroacetate;    -   1-[4-(3-Aminomethyl-phenyl)-4-hydroxy-piperidin-1-yl]-1-(5-phenethyl-pyridin-3-yl)-methanone-ditrifluoroacetate;    -   1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(1-methyl-1H-indol-3-yl)-methanone-trifluoroacetate;    -   1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(2-fluoro-phenylethynyl)-phenyl]-methanone        trifluoroacetate;    -   1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[2-(2-fluoro-phenyl)-ethyl]-phenyl-methanone        trifluoroacetate;    -   1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-3-[2-(6-amino-pyridin-3-yl)-ethyl]-phenyl}-methanone        tri-trifluoroacetate;    -   1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(6-chloro-thieno[3,2-b]thiophen-2-yl)-methanone        trifluoroacetate;    -   (3R,4S) and (3S,        4R)-4-(3-Aminomethyl-phenyl)-1-(5-phenethyl-pyridine-3-carbonyl)-piperidine-3-carboxylic        acid ethyl ester dihydrochloride;    -   3-[1-(5-Phenylethynyl-furan-2-carbonyl)-piperidin-4-yl]-benzylamine        trifluoroacetate;    -   4-(3-Aminomethyl-phenyl)-piperidine-1-carboxylic acid        (3,4-dichloro-phenyl)-amide trifluoroacetate;    -   1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(2,3-dihydro-benzofuran-5-yl)-methanone;    -   1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(5        ,6-dichloro-pyridin-3-yl)-methanone;    -   1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(3-bromo-4-fluoro-phenyl)-methanone;    -   (E)-1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-3-(2-nitro-phenyl)-propenone;    -   1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(3-bromo-5-iodo-phenyl)-methanone;    -   (E)-1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-3-phenyl-propenone;    -   1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-3-cyclohexyl-propan-1-one;        and the corresponding N-oxides, and their prodrugs; and        pharmaceutically acceptable salts and solvates (e.g. hydrates)        of such compounds and their N-oxides and prodrugs.

Pharmaceutical Compositions

As explained above, compounds of the present invention exhibit usefulpharmacological activity and accordingly are incorporated intopharmaceutical compositions and used in the treatment of patientssuffering from certain medical disorders. The present invention thusprovides, according to a further aspect, compounds of the invention andpharmaceutical compositions containing compounds of the invention foruse in therapy, wherein a pharmaceutical composition of the presentinvention comprising a compound of the present invention, and apharmaceutically acceptable carrier thereof. As used herein, the term“pharmaceutically acceptable” preferably means approved by a regulatoryagency of a government, in particular the Federal government or a stategovernment, or listed in the U.S. Pharmacopeia or another generallyrecognized pharmacopeia for use in animals, and more particularly inhumans. Suitable pharmaceutical carriers are described in “Remington'sPharmaceutical Sciences” by E. W. Martin.

A pharmaceutical composition according to the present invention can beprepared according to the customary methods, using one or morepharmaceutically acceptable adjuvants or excipients. The adjuvantscomprise, inter alia, diluents, sterile aqueous media and the variousnon-toxic organic solvents. The compositions may be presented in theform of tablets, pills, granules, powders, aqueous solutions orsuspensions, injectable solutions, elixirs or syrups, and can containone or more agents chosen from the group comprising sweeteners,flavorings, colorings, or stabilizers in order to obtainpharmaceutically acceptable preparations. The choice of vehicle and thecontent of active substance in the vehicle are generally determined inaccordance with the solubility and chemical properties of the activecompound, the particular mode of administration and the provisions to beobserved in pharmaceutical practice. For example, excipients such aslactose, sodium citrate, calcium carbonate, dicalcium phosphate anddisintegrating agents such as starch, alginic acids and certain complexsilicates combined with lubricants such as magnesium stearate, sodiumlauryl sulfate and talc may be used for preparing tablets. To prepare acapsule, it is advantageous to use lactose and high molecular weightpolyethylene glycols. When aqueous suspensions are used they can containemulsifying agents or agents which facilitate suspension. Diluents suchas sucrose, ethanol, polyethylene glycol, propylene glycol, glycerol andchloroform or mixtures thereof may also be used. Such pharmaceuticallyacceptable carriers can also be sterile water and oils, including thoseof petroleum, animal, vegetable or synthetic origin, such as peanut oil,soybean oil, mineral oil, sesame oil and the like. Water is a preferredcarrier when the pharmaceutical composition is administeredintravenously. Saline solutions and aqueous dextrose and glycerolsolutions can also be employed as liquid carriers, particularly forinjectable solutions. Suitable pharmaceutical excipients includemannitol, human serum albumin (HSA), starch, glucose, lactose, sucrose,gelatin, malt, rice, flour, chalk, silica gel, magnesium carbonate,magnesium stearate, sodium stearate, glycerol monostearate, talc, sodiumchloride, dried skim milk, glycerol, propylene, glycol, water, ethanoland the like. These compositions can take the form of solutions,suspensions, tablets, pills, capsules, powders, sustained-releaseformulations and the like.

Naturally, a pharmaceutical composition of the present inventioncompositions will contain an effective diagnostic or therapeutic amountof the active compound together with a suitable amount of carrier so asto provide the form for proper administration to the patient. Whileintravenous injection is a very effective form of administration, othermodes can be employed, such as by injection, or by oral, nasal orparenteral administration, which are discussed infra.

Methods of Treatment

Compounds within the scope of the present invention possess tryptaseinhibition activity according to tests described in the literature anddescribed in vitro procedures hereinafter, and which test results arebelieved to correlate to pharmacological activity in humans and othermammals. Thus, in a further embodiment, the present invention providescompounds of the invention and compositions containing compounds of theinvention for use in the treatment of a patient suffering from, orsubject to, conditions that can be ameliorated by the administration ofan inhibitor of tryptase. For example, compounds of the presentinvention are useful in the treatment of inflammatory diseases, forexample joint inflammation, including arthritis, rheumatoid arthritisand other arthritic conditions such as rheumatoid spondylitis, goutyarthritis, traumatic arthritis, rubella arthritis, psoriatic arthritis,osteoarthritis and other chronic inflammatory joint diseases, ordiseases of joint cartilage destruction, ocular conjunctivitis, vernalconjunctivitis, inflammatory bowel disease, asthma, allergic rhinitis,interstitial lung diseases, fibrosis, sceleroderma, pulmonary fibrosis,liver cirrhosis, myocardial fibrosis, neurofibromas, hypertrophic scars,various dermatological conditions, for example, atopic dermatitis andpsoriasis, myocardial infarction, stroke, angina and other consequencesof atherosclerotic plaque rupture, as well as periodontal disease,diabetic retinopathy, tumor growth, anaphylaxis, multiple sclerosis,peptic ulcers, and syncytial viral infections.

A special embodiment of the therapeutic methods of the present inventionis the treating of asthma.

Another special embodiment of the therapeutic methods of the presentinvention is the treating of joint inflammation.

Another special embodiment of the therapeutic methods of the presentinvention is the treating of inflammatory bowel disease.

According to a further feature of the invention there is provided amethod for the treatment of a human or animal patient suffering from, orsubject to, conditions which can be ameliorated by the administration ofan inhibitor of tryptase, for example conditions as hereinbeforedescribed, which comprises the administration to the patient of aneffective amount of compound of the invention or a compositioncontaining a compound of the invention. “Effective amount” is meant todescribe an amount of compound of the present invention effective ininhibiting tryptase and thus producing the desired therapeutic effect.

Combination Therapy

As explained above, other pharmaceutically active agents can be employedin combination with the compounds of the invention depending upon thedisease being treated. For example, in the treatment of asthma,beta-adrenergic agonists such as albuterol, terbutaline, formoterol,fenoterol or prenaline can be included, as can anticholinergics such asipratropium bromide, anti-inflammatory corticosteroids such asbeclomethasone dipropionate, triamcinolone acetonide, flunisolide ordexamethasone, and anti-inflammatory agents such as sodium cromoglycateand nedocromil sodium. Thus, the present invention extends to apharmaceutical composition comprising a compound of the presentinvention and a second compound selected from the group consisting of abeta andrenergic agonist, an anticholinergic, an anti-inflammatorycorticosteroid, and an anti-inflammatory agent; and a pharmaceuticallyacceptable carrier thereof. Particular pharmaceutical carriers havingapplications in this pharmaceutical composition are described herein.

Furthermore, the present invention extends to a method for treating apatient suffering from asthma, comprising administering the patient acompound of the present invention, and a second compound selected fromthe group consisting of a beta andrenergic agonist, an anticholinergic,an anti-inflammatory corticosteroid, and an anti-inflammatory agent. Insuch a combination method, a compound of the present invention can beadministered prior to the administration of the second compound, acompound of the present invention can be administered afteradministration of the second compound, or a compound of the presentinvention and the second compound can be administered concurrently.

Modes of Delivery

According to the invention, a compound of the present invention, or apharmaceutical composition of the present invention, may be introducedparenterally, transmucosally, e.g., orally, nasally, pulmonarily, orrectally, or transdermally to a patient.

Oral Delivery

Contemplated for use herein are oral solid dosage forms, which aredescribed generally in Remington's Pharmaceutical Sciences, 18th Ed.1990(Mack Publishing Co. Easton Pa. 18042) at Chapter 89, which is hereinincorporated by reference. Solid dosage forms include tablets, capsules,pills, troches or lozenges, cachets or pellets. Also, liposomal orproteinoid encapsulation may be used to formulate the presentcompositions (as, for example, proteinoid microspheres reported in U.S.Pat. No.4,925,673). Liposomal encapsulation may be used and theliposomes may be derivatized with various polymers (e.g., U.S. Pat. No.5,013,556). A description of possible solid dosage forms for atherapeutic is given by Marshall, K. In: Modern Pharmaceutics Edited byG. S. Banker and C. T. Rhodes Chapter 10, 1979, herein incorporated byreference. In general, the formulation will include a compound of thepresent invention, and inert ingredients which allow for protectionagainst the stomach environment, and release of the biologically activematerial, i.e., a compound of the present invention, in the intestine.

Also specifically contemplated are oral dosage forms of a compound ofthe present invention. Such a compound may be chemically modified sothat oral delivery is more efficacious. Generally, the chemicalmodification contemplated is the attachment of at least one moiety tothe component molecule itself, where said moiety permits (a) inhibitionof proteolysis; and (b) uptake into the blood stream from the stomach orintestine. Also desired is the increase in overall stability of thecompound of the present invention, and increase in circulation time inthe body. Examples of such moieties include: polyethylene glycol,copolymers of ethylene glycol and propylene glycol, carboxymethylcellulose, dextran, polyvinyl alcohol, polyvinyl pyrrolidone andpolyproline. Abuchowski and Davis, 1981, “Soluble Polymer-EnzymeAdducts” In: Enzymes as Drugs, Hocenberg and Roberts, eds.,Wiley-Interscience, New York, N.Y., pp.367-383; Newmark, et al., 1982,J. Appl. Biochem. 4:185-189. Other polymers that could be used arepoly-1,3-dioxolane and poly-1,3,6-tioxocane. Preferred forpharmaceutical usage, as indicated above, are polyethylene glycolmoieties.

For a compound of the present invention, the location of release may bethe stomach, the small intestine (the duodenum, the jejunum, or theileum), or the large intestine. One skilled in the art has availableformulations that will not dissolve in the stomach, yet will release thematerial in the duodenum or elsewhere in the intestine. Preferably, therelease will avoid the deleterious effects of the stomach environment,either by protection of the compound of the present invention, or byrelease of the compound beyond the stomach environment, such as in theintestine.

To ensure full gastric resistance a coating impermeable to at least pH5.0 is essential. Examples of the more common inert ingredients that areused as enteric coatings are cellulose acetate trimellitate (CAT),hydroxypropylmethylcellulose phthalate (HPMCP), HPMCP 50, HPMCP 55,polyvinyl acetate phthalate (PVAP), Eudragit L30D, Aquateric, celluloseacetate phthalate (CAP), Eudragit L, Eudragit S, and shellac. Thesecoatings may be used as mixed films.

A coating or mixture of coatings can also be used on tablets, which arenot intended for protection against the stomach. This can include sugarcoatings, or coatings that make the tablet easier to swallow. Capsulesmay consist of a hard shell (such as gelatin) for delivery of drytherapeutic i.e. powder; for liquid forms, a soft gelatin shell may beused. The shell material of cachets could be thick starch or otheredible paper. For pills, lozenges, molded tablets or tablet triturates,moist massing techniques can be used.

The therapeutic can be included in the formulation as finemulti-particulates in the form of granules or pellets of particle sizeabout 1 mm. The formulation of the material for capsule administrationcould also be as a powder, lightly compressed plugs or even as tablets.The therapeutic could be prepared by compression.

Colorants and flavoring agents may all be included. For example, thecompound of the present invention may be formulated (such as by liposomeor microsphere encapsulation) and then further contained within anedible product, such as a refrigerated beverage containing colorants andflavoring agents.

One may dilute or increase the volume of the therapeutic with an inertmaterial. These diluents could include carbohydrates, especiallymannitol, α-lactose, anhydrous lactose, cellulose, sucrose, modifieddextrans and starch. Certain inorganic salts may be also be used asfillers including calcium triphosphate, magnesium carbonate and sodiumchloride. Some commercially available diluents are Fast-Flo, Emdex,STA-Rx 1500, Emcompress and Avicell.

Disintegrants may be included in the formulation of the therapeutic intoa solid dosage form. Materials used as disintegrates include, but arenot limited to starch, including the commercial disintegrant based onstarch, Explotab. Sodium starch glycolate, Amberlite, sodiumcarboxymethylcellulose, ultramylopectin, sodium alginate, gelatin,orange peel, acid carboxymethyl cellulose, natural sponge and bentonitemay all be used. Another form of the disintegrants are the insolublecationic exchange resins. Powdered gums may be used as disintegrants andas binders and these can include powdered gums such as agar, Karaya ortragacanth. Alginic acid and its sodium salt are also useful asdisintegrants.

Binders may be used to hold the therapeutic agent together to form ahard tablet and include materials from natural products such as acacia,tragacanth, starch and gelatin. Others include methyl cellulose (MC),ethyl cellulose (EC) and carboxymethyl cellulose (CMC). Polyvinylpyrrolidone (PVP) and hydroxypropylmethyl cellulose (HPMC) could both beused in alcoholic solutions to granulate the therapeutic.

An anti-frictional agent may be included in the formulation of thetherapeutic to prevent sticking during the formulation process.Lubricants may be used as a layer between the therapeutic and the diewall, and these can include but are not limited to; stearic acidincluding its magnesium and calcium salts, polytetrafluoroethylene(PTFE), liquid paraffin, vegetable oils and waxes. Soluble lubricantsmay also be used such as sodium lauryl sulfate, magnesium laurylsulfate, polyethylene glycol of various molecular weights, Carbowax 4000and 6000.

Glidants that might improve the flow properties of the drug duringformulation and to aid rearrangement during compression might be added.The glidants may include starch, talc, pyrogenic silica and hydratedsilicoaluminate.

To aid dissolution of the therapeutic into the aqueous environment asurfactant might be added as a wetting agent. Surfactants may includeanionic detergents such as sodium lauryl sulfate, dioctyl sodiumsulfosuccinate and dioctyl sodium sulfonate. Cationic detergents mightbe used and could include benzalkonium chloride or benzethomiumchloride. The list of potential non-ionic detergents that could beincluded in the formulation as surfactants are lauromacrogol 400,polyoxyl 40 stearate, polyoxyethylene hydrogenated castor oil 10, 50 and60, glycerol monostearate, polysorbate 40, 60, 65 and 80, sucrose fattyacid ester, methyl cellulose and carboxymethyl cellulose. Thesesurfactants could be present in the formulation of a compound of thepresent invention either alone or as a mixture in different ratios.

Additives which potentially enhance uptake of a compound of the presentinvention are, for instance, the fatty acids oleic acid, linoleic acidand linolenic acid.

Controlled release oral formulation may be desirable. The drug could beincorporated into an inert matrix which permits release by eitherdiffusion or leaching mechanisms, e.g., gums. Slowly degeneratingmatrices may also be incorporated into the formulation. Some entericcoatings also have a delayed release effect.

Another form of a controlled release of this therapeutic is by a methodbased on the Oros therapeutic system (Alza Corp.), i.e. the drug isenclosed in a semipermeable membrane which allows water to enter andpush drug out through a single small opening due to osmotic effects.Other coatings may be used for the formulation. These include a varietyof sugars which could be applied in a coating pan. The therapeutic agentcould also be given in a film coated tablet and the materials used inthis instance are divided into 2 groups. The first are the nonentericmaterials and include methyl cellulose, ethyl cellulose, hydroxyethylcellulose, methylhydroxy-ethyl cellulose, hydroxypropyl cellulose,hydroxypropyl-methyl cellulose, sodium carboxy-methyl cellulose,providone and the polyethylene glycols. The second group consists of theenteric materials that are commonly esters of phthalic acid.

A mix of materials might be used to provide the optimum film coating.Film coating may be carried out in a pan-coater or in a fluidized bed orby compression coating.

Pulmonary Delivery

Also contemplated herein is pulmonary delivery of a compound of thepresent invention, either alone, or in a pharmaceutical composition. Thecompound is delivered to the lungs of a mammal while inhaling andtraverses across the lung epithelial lining to the blood stream. Otherreports of this include Adjei et al., 1990, Pharmaceutical Research,7:565-569; Adjei et al., 1990, International Journal of Pharmaceutics,63:135-144 (leuprolide acetate); Braquet et al., 1989, Journal ofCardiovascular Pharmacology, 13(suppl. 5):143-146 (endothelin-1);Hubbard et al., 1989, Annals of Internal Medicine, Vol. III, pp. 206-212(a1-antitrypsin); Smith et al., 1989, J. Clin. Invest. 84:1145-1146(a-1-proteinase); Oswein et al., 1990, “Aerosolization of Proteins”,Proceedings of Symposium on Respiratory Drug Delivery II, Keystone,Colorado, March, (recombinant human growth hormone); Debs et al., 1988,J. Immunol. 140:3482-3488 (interferon-γ and tumor necrosis factor alpha)and Platz et al., U.S. Pat. No. 5,284,656 (granulocyte colonystimulating factor). A method and composition for pulmonary delivery ofdrugs for systemic effect is described in U.S. Pat. No.5,451,569, issuedSep. 19, 1995 to Wong et al.

Contemplated for use in the practice of this invention are a wide rangeof mechanical devices designed for pulmonary delivery of therapeuticproducts, including but not limited to nebulizers, metered doseinhalers, and powder inhalers, all of which are familiar to thoseskilled in the art.

Some specific examples of commercially available devices suitable forthe practice of this invention are the Ultravent nebulizer, manufacturedby Mallinckrodt, Inc., St. Louis, Mo.; the Acorn II nebulizer,manufactured by Marquest Medical Products, Englewood, Colo.; theVentolin metered dose inhaler, manufactured by Glaxo Inc., ResearchTriangle Park, N.C.; and the Spinhaler powder inhaler, manufactured byFisons Corp., Bedford, Mass., to name only a few. All such devicesrequire the use of formulations suitable for the dispensing a compoundof the present invention. Typically, each formulation is specific to thetype of device employed and may involve the use of an appropriatepropellant material, in addition to the usual diluents, adjuvants and/orcarriers useful in therapy. Also, the use of liposomes, microcapsules ormicrospheres, inclusion complexes, or other types of carriers iscontemplated. Chemically modified compounds of the present invention mayalso be prepared in different formulations depending on the type ofchemical modification or the type of device employed.

Formulations suitable for use with a nebulizer, either jet orultrasonic, will typically comprise a compound of the present inventiondissolved in water at a concentration of about 0.1 to 25 mg of compoundper mL of solution. The formulation may also include a buffer and asimple sugar (e.g., for stabilization and regulation of osmoticpressure). The nebulizer formulation may also contain a surfactant, toreduce or prevent surface induced aggregation of the compound caused byatomization of the solution in forming the aerosol.

Formulations for use with a metered-dose inhaler device will generallycomprise a finely divided powder containing a compound of the inventionsuspended in a propellant with the aid of a surfactant. The propellantmay be any conventional material employed for this purpose, such as achlorofluorocarbon, a hydrochlorofluorocarbon, a hydrofluorocarbon, or ahydrocarbon, including trichlorofluoromethane, dichlorodifluoromethane,dichlorotetrafluoroethanol, and 1,1,1,2-tetrafluoroethane, orcombinations thereof. Suitable surfactants include sorbitan trioleateand soya lecithin. Oleic acid may also be useful as a surfactant.

Formulations for dispensing from a powder inhaler device will comprise afinely divided dry powder containing a compound of the invention, andmay also include a bulking agent, such as lactose, sorbitol, sucrose, ormannitol in amounts which facilitate dispersal of the powder from thedevice, e.g., 50 to 90% by weight of the formulation. The compound ofthe present invention should most advantageously be prepared inparticulate form with an average particle size of less than 10 mm (ormicrons), most preferably 0.5 to 5 mm, for most effective delivery tothe distal lung.

Nasal Delivery

Nasal delivery of a compound of the present invention is alsocontemplated. Nasal delivery allows the passage of the compound to theblood stream directly after administering the therapeutic product to thenose, without the necessity for deposition of the product in the lung.Formulations for nasal delivery include those with dextran orcyclodextran.

Transdermal Delivery

Various and numerous methods are known in the art for transdermaladministration of a drug, e.g., via a transdermal patch, haveapplications in the present invention. Transdermal patches are describedin for example, U.S. Pat. No. 5,407,713, issued Apr. 18, 1995 to Rolandoet al.; U.S. Pat. No. 5,352,456, issued Oct. 4, 1004 to Fallon et al.;U.S. Pat. No. 5,332,213 issued Aug. 9, 1994 to D'Angelo et al.; U.S.Pat. No. 5,336,168, issued Aug. 9, 1994 to Sibalis; U.S. Pat. No.5,290,561, issued Mar. 1, 1994 to Farhadieh et al.; U.S. Pat. No.5,254,346, issued Oct. 19, 1993 to Tucker et al.; U.S. Pat. No.5,164,189, issued Nov. 17, 1992 to Berger et al.; U.S. Pat. No.5,163,899, issued Nov. 17, 1992 to Sibalis; U.S. Pat. Nos. 5,088,977 and5,087,240, both issued Feb. 18, 1992 to Sibalis; U.S. Pat. No.5,008,110, issued Apr. 16, 1991 to Benecke et al.; and U.S. Pat. No.4,921,475, issued May 1, 1990 to Sibalis, the disclosure of each ofwhich is incorporated herein by reference in its entirety.

It can be readily appreciated that a transdermal route of administrationmay be enhanced by use of a dermal penetration enhancer, e.g., such asenhancers described in U.S. Pat. No. 5,164,189 (supra), U.S. Pat. No.5,008,110 (supra), and U.S. Pat. No. 4,879,119, issued Nov. 7, 1989 toAruga et al., the disclosure of each of which is incorporated herein byreference in its entirety.

Topical Administration

For topical administration, gels (water or alcohol based), creams orointments containing compounds of the invention may be used. Compoundsof the invention may also be incorporated in a gel or matrix base forapplication in a patch, which would allow a controlled release ofcompound through the transdermal barrier.

Rectal Administration

Solid compositions for rectal administration include suppositoriesformulated in accordance with known methods and containing at least onecompound of the invention.

The percentage of active ingredient in the compositions of the inventionmay be varied, it being necessary that it should constitute a proportionsuch that a suitable dosage shall be obtained. Obviously, several unitdosage forms may be administered at about the same time. The doseemployed will be determined by the physician, and depends upon thedesired therapeutic effect, the route of administration and the durationof the treatment, and the condition of the patient. In the adult, thedoses are generally from about 0.001 to about 50, preferably about 0.001to about 5, mg/kg body weight per day by inhalation, from about 0.01 toabout 100, preferably 0.1 to 70, more especially 0.5 to 10, mg/kg bodyweight per day by oral administration, and from about 0.001 to about 10,preferably 0.01 to 1, mg/kg body weight per day by intravenousadministration. In each particular case, the doses will be determined inaccordance with the factors distinctive to the subject to be treated,such as age, weight, general state of health and other characteristicswhich can influence the efficacy of the medicinal product.

Furthermore, compounds according to the invention may be administered asfrequently as necessary in order to obtain the desired therapeuticeffect. Some patients may respond rapidly to a higher or lower dose andmay find much weaker maintenance doses adequate. For other patients, itmay be necessary to have long-term treatments at the rate of 1 to 4doses per day, in accordance with the physiological requirements of eachparticular patient. Generally, the active product may be administeredorally 1 to 4 times per day. Of course, for some patients, it will benecessary to prescribe not more than one or two doses per day.

Naturally, a patient in whom administration of a compound of the presentinvention is an effective therapeutic regimen is preferably a human, butcan be any animal. Thus, as can be readily appreciated by one ofordinary skill in the art, the methods and pharmaceutical compositionsof the present invention are particularly suited to administration toany animal, particularly a mammal, and including, but by no meanslimited to, domestic animals, such as feline or canine subjects, farmanimals, such as but not limited to bovine, equine, caprine, ovine, andporcine subjects, wild animals (whether in the wild or in a zoologicalgarden), research animals, such as mice, rats, rabbits, goats, sheep,pigs, dogs, cats, etc., avian species, such as chickens, turkeys,songbirds, etc., i.e., for veterinary medical use.

Preparation of Compounds of the Invention

Compounds of the invention may be prepared by the application oradaptation of known methods, by which is meant methods used heretoforeor described in the literature, for example those described by R. C.Larock in Comprehensive Organic Transformations, VCH publishers, 1989.

In the reactions described hereinafter it may be necessary to protectreactive functional groups, for example hydroxy, amino, imino, thio orcarboxy groups, where these are desired in the final product, to avoidtheir unwanted participation in the reactions. Conventional protectinggroups may be used in accordance with standard practice, for examplessee T. W. Greene and P. G. M. Wuts in “Protective Groups in OrganicChemistry” John Wiley and Sons, 1991.Compounds of formula (Ia) whereinR³, R⁴, R⁵ and n are as hereinbefore defined, R¹ and R² are bothhydrogen and

is a single bond, represented by formula (IX), may be prepared as shownin Scheme 1

For example compounds of formula (IX) may be prepared by:

-   -   (i) treating compounds of formula (II) wherein R⁴ and n are as        hereinbefore defined and P¹ is a suitable protecting group, such        as benzyloxycarbonyl, with a suitable base, such as lithium        hexamethyldisilazane, in an inert solvent, such as        tetrahydrofuran, and at a temperature at about −78° C., followed        by reaction with N-phenyltrifluoromethane-sulfonimide to give        compounds of formula (III) wherein R⁴, P¹ and n are as        hereinbefore defined and Tf is —SO₂CF₃;    -   (ii) reaction of triflates of formula (III) with an aryl boronic        acid of formula (X):    -    in the presence of an aqueous base such as sodium bicarbonate        and a palladium catalyst such as palladium        tetrakistriphenylphosphine, and at a temperature from about 80        to about 100° C., to give compounds of formula (IV) wherein R⁴,        R⁵, P¹ and n are as hereinbefore defined;    -   (iii) reduction of compounds of formula (IV) with sodium        borohydride in ethanol to give compounds of formula (V) wherein        R⁴, R⁵, P¹ and are as hereinbefore defined;    -   (iv) conversion of the hydroxymethyl group in compounds of        formula (V) to an aminomethyl group which is suitably protected        to facilitate the further processes described hereinafter—for        example reaction of compounds of formula (V) with phosphorus        tribromide in pyridine followed by treatment of the resultant        bromomethyl intermediate with di-tert-butyliminodicarboxylate to        give compounds of formula (VI) wherein R⁴, R⁵, P¹ and n are as        hereinbefore defined and P² and P³ are each        tertiary-butyloxycarbonyl (a suitable protecting group that is        stable under conditions for the subsequent removal of protecting        group P¹);    -   (v) removal of the protecting group P¹ in compounds of formula        (VI), for example when P¹ is benzyloxycarbonyl and P² and P³ are        both tertiary-butyloxycarbonyl, the deprotection may        conveniently be carried out by hydrogenation in the presence of        a suitable metal catalyst, e.g. platinum or palladium optionally        supported on an inert carrier such as carbon, preferably in a        solvent such as methanol or ethanol to give compounds of        formula (VII) wherein R⁴, R⁵ and n are as hereinbefore defined        and P² and P³ are as just defined;    -   (vi) reaction of compounds of formula (VII) with compounds of        formula (XI):    -    wherein R³ is as hereinbefore defined and X¹ is a hydroxy        group, or a halogen, preferably chlorine, atom using standard        coupling conditions [for example when X¹ is a hydroxy group the        reaction may be carried out using standard peptide coupling        procedures for example coupling in the presence of        O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium        hexafluorophosphate and triethylamine (or diisopropylethylamine)        in tetrahydrofuran (or dimethylformamide), at room temperature;        and when X¹ is a halogen atom the acylation reaction may be        carried out with the aid of a base, such pyridine, preferably in        a solvent such as tetrahydrofuran and at a temperature at about        room temperature] to give compounds of formula (VIII) wherein        R³, R⁴, R⁵, n, P² and P³ are as defined above;    -   (vii) removal of the protecting groups P² and P³ in compounds of        formula (VIII), for example when P² and P³ are both        tertiary-butyloxycarbonyl the reaction may conveniently be        carried out in the presence of an acid such as trifluoracetic        acid in an inert solvent, such as dichloromethane, or by        treatment with hydrogen chloride in methanol. Compounds of        formula (Ia) wherein R¹, R², R³, R⁴, R⁵ and n are as        hereinbefore defined and        is a single bond, represented by formula (XVI), may be prepared        as shown in scheme 2.

For example compounds of formula (XVI) may be prepared by:

-   -   (i) reaction of compounds of formula (II) wherein R⁴ and n are        as hereinbefore defined and P¹ is a suitable protecting group,        such as benzyloxycarbonyl, with an aryl boronate of formula        (XVII):    -    wherein R¹, R², P² and P³ are as hereinbefore defined in the        presence of potassium carbonate and a palladium catalyst such as        [1,1′-bis-(diphenylphosphino)ferroceno]-dichloropalladium        (II)-dichloromethane complex in an inert solvent, such as        dimethylsulfoxide, and at a temperature at about 80° C. to give        compounds of formula (XII) wherein R¹, R², R⁴, R⁵, n, P¹, P² and        P³ are as hereinbefore defined; alternatively compounds of        formula (XII) may be prepared by reaction of compounds of        formula (II) with bis(pinacolato)boron in the presence of        potassium acetate, (diphenylphosphino)-ferrocene and        [1,1′-bis-(diphenylphosphino)ferroceno]-dichloropalladium (II),        in an inert solvent, such as dioxane, and at a temperature at        about 80° C. followed by reaction of the intermediate boronate        of formula (XIII) with compounds of formula (XVIII):    -    wherein R¹, R², P¹ and P² are as hereinbefore defined in the        presence of potassium carbonate and a palladium catalyst such as        [1,1′-bis-(diphenylphosphino)ferroceno]-dichloropalladium        (II)-dichloromethane complex in an inert solvent, such as        dimethylsulfoxide, and at a temperature at about 80° C.];    -   (ii) removal of the protecting group P¹ in compounds of formula        (XII), for example when P¹ is benzyloxycarbonyl and P² and P³        are both tertiary-butyloxycarbonyl, the deprotection may        conveniently be carried out by hydrogenation as described        hereinabove to give compounds of formula (XIV) wherein R¹, R²,        R⁴, R⁵, n, P² and P³ are as just defined;    -   (iii) reaction of compounds of formula (XIV) with compounds of        formula (XI) wherein R¹ is as hereinbefore defined and X¹ is a        hydroxy group, or a halogen, preferably chlorine, atom using        standard coupling conditions [for example those described        hereinabove] to give compounds of formula (XV) wherein R¹, R²,        R³, R⁴, R⁵, n, P² and P³ are as defined above;    -   (vii) removal of the protecting groups P² and P³ in compounds of        formula (XV), using standard coupling conditions [for example        those described hereinabove].        Compounds of formula (Ia) wherein R¹, R², R³, R⁴, R⁵ and n are        as hereinbefore defined and        is a single bond, represented by formula (XVI), may also be        prepared using resin technology as shown in scheme 3:

For example compounds of formula (XVI) may be prepared by:

-   -   (i) Coupling of the resin (XIX, an aminomethylated        styrene/divinylbenzene copolymer), where        represents the polymeric core (comprising polystyrene        crosslinked with 1% to 2% divinylbenzene), with        4-hydroxy-2,3,5,6-tetrafluorobenzoic acid, according to the        procedure described by J. M. Salvino et. al. in International        Patent Application Publication No. WO 99/67228, to give TFP        resin wherein        is as hereinbefore defined;    -   (ii) treatment of TFP resin with acids of formula (XI) wherein        R³ is as hereinbefore defined and X¹ is hydroxy, in the presence        of diisopropyl carbodiimide and dimethylaminopyridine, in an        inert solvent, such as dimethylformamide, and at a temperature        at about room temperature, to give resin 1 wherein R³ and        are hereinbefore defined;    -   (iii) treatment of resin 1 with compounds of formula (XIV)        wherein R¹, R², R⁴, R⁵, n, P¹ and P² are as defined immediately        hereinbefore, in an inert solvent, such as dichloromethane, and        at a temperature at about room temperature, to give compounds of        formula (XV);    -   (iv) removal of the protecting groups in compounds of formula        (XV), for example when P² and P³ are both        tertiary-butyloxycarbonyl the reaction may conveniently be        carried out in the presence of an acid such as trifluoracetic        acid in an inert solvent, such as dichloromethane, or by        treatment with hydrogen chloride in methanol.        Compounds of formula (Ib), wherein R³ and R⁵ are as hereinbefore        defined and R⁴ is cyano attached at the 4 position of the        piperidine ring, represented by formula (XX), may be prepared as        shown in scheme 4:

For example compounds of formula (XX) may be prepared by:

-   -   (i) Reacting a benzyl bromide of formula (XXI) wherein R⁵ is as        hereinbefore defined, with sodium cyanide, in the presence of a        phase transfer catalyst, such as tetrabutylammonium bromide, in        a mixture of water and an inert solvent, such as        dichloromethane, and at a temperature at about room temperature        to give compounds of formula (XXII) wherein R⁵ is as        hereinbefore defined;    -   (ii) treatment of the benzylcyanides of formula (XXII) with a        suitably protected bis-(2-haloethyl)amine of formula (XXVIII):    -    wherein X is halo, preferably chloro, and P¹ is a suitable        protecting group, such as tertiary-butyloxycarbonyl, in the        presence of sodium hydride and in an inert solvent, such as        dimethylformamide, and at a temperature at about room        temperature, to give compounds of formula (XXIII) wherein R⁵ and        P¹ are as hereinbefore defined;    -   (iii) hydrogenation of compounds of formula (XXIII) in the        presence of hydrochloric acid in ethanol and under pressure to        give compounds of formula (XXIV) wherein R⁵ and P¹ are as        hereinbefore defined;    -   (iv) protection of the amino group in compounds of        formula (XXIV) with a suitable protecting group, for example        with a benzyloxycarbonyl group, to give compounds of        formula (XXV) wherein R⁵, P¹ and P² are as hereinbefore defined;    -   (v) removal of the protecting group P¹ in compounds of        formula (XXV) to give compounds of formula (XXVI) wherein R⁵ and        P² are as hereinbefore defined;    -   (vi) reaction of compounds of formula (XXVI) with compounds of        formula (XI) wherein R¹ is as hereinbefore defined and X¹ is a        hydroxy group, or a halogen, preferably chlorine, atom using        standard coupling conditions [for example those described        hereinabove] to give compounds of formula (XXVII) wherein R⁵ and        P² are as defined above;    -   (vii) removal of the protecting groups P² in compounds of        formula (XXVII), using standard coupling conditions [for example        those described hereinabove].

Compounds of formula (Ia) wherein R³, R⁴, R⁵ and n are as hereinbeforedefined, R¹ and R² are both hydrogen and

is a double bond, represented by formula (IX), may be prepared byremoval of the P¹ protecting group in compounds of formula (VI) followedby acylation with compounds of formula (XI) and subsequent removal ofthe P² and P³ protecting groups.

Compounds of formula (Ia) wherein R¹, R², R³, R⁴, R⁵ and n are ashereinbefore defined and

is a double bond, represented by formula (XVI), may be prepared byremoval of the P¹ protecting group in compounds of formula (XII)followed by acylation with compounds of formula (XI) and subsequentremoval of the P² and P³ protecting groups.

According to a further feature of the present invention, compounds ofthe invention may be prepared by interconversion of other compounds ofthe invention.

As an example of the interconversion process, compounds of formula (Ia)wherein R¹, R², R⁴, R⁵ and n are as hereinbefore defined and R³ containsan optionally substituted alkylene linkage, may be prepared byhydrogenation of the corresponding compounds of formula (Ia) in which R³contains the corresponding optionally substituted alkenylene oralkynylene linkage. The hydrogenation may be carried out using hydrogen(optionally under pressure) in the presence of a suitable metalcatalyst, e.g. platinum or palladium optionally supported on an inertcarrier such as carbon, preferably in a solvent such as methanol orethanol, and at a temperature at about room temperature.

As another example of the interconversion process, compounds of theinvention containing a heterocyclic group wherein the heteroatom is anitrogen atom may be oxidized to their corresponding N-oxides. Theoxidation may conveniently be carried out by means of reaction with amixture of hydrogen peroxide and an organic acid, e.g. acetic acid,preferably at or above room temperature, for example at a temperature ofabout 60-90° C. Alternatively, the oxidation may be carried out byreaction with a peracid, for example peracetic acid orm-chloroperoxybenzoic acid, in an inert solvent such as chloroform ordichloromethane, at a temperature from about room temperature to reflux,preferably at elevated temperature. The oxidation may alternatively becarried out by reaction with hydrogen peroxide in the presence of sodiumtungstate at temperatures between room temperature and about 60° C.

As another example of the interconversion process, compounds of formula(Ia) containing sulfone linkages may be prepared by the oxidation ofcorresponding compounds containing —S— or sulfoxide linkages. Forexample, the oxidation may conveniently be carried out by means ofreaction with a peroxyacid, e.g. 3-chloroperbenzoic acid, preferably inan inert solvent, e.g. dichloromethane, preferably at or near roomtemperature.

It will be appreciated that compounds of the present invention maycontain asymmetric centers. These asymmetric centers may independentlybe in either the R or S configuration. It will be apparent to thoseskilled in the art that certain compounds of the invention may alsoexhibit geometrical isomerism. It is to be understood that the presentinvention includes individual geometrical isomers and stereoisomers andmixtures thereof, including racemic mixtures, of compounds the presentinvention. Such isomers can be separated from their mixtures, by theapplication or adaptation of known methods, for example chromatographictechniques and recrystallisation techniques, or they are separatelyprepared from the appropriate isomers of their intermediates.

According to a further feature of the invention, acid addition salts ofthe compounds of this invention may be prepared by reaction of the freebase with the appropriate acid, by the application or adaptation ofknown methods. For example, the acid addition salts of the compounds ofthis invention may be prepared either by dissolving the free base inwater or aqueous alcohol solution or other suitable solvents containingthe appropriate acid and isolating the salt by evaporating the solution,or by reacting the free base and acid in an organic solvent, in whichcase the salt separates directly or can be obtained by concentration ofthe solution.

The acid addition salts of the compounds of this invention can beregenerated from the salts by the application or adaptation of knownmethods. For example, parent compounds of the invention can beregenerated from their acid addition salts by treatment with an alkali,e.g. aqueous sodium bicarbonate solution or aqueous ammonia solution.

The starting materials and intermediates may be prepared by theapplication or adaptation of known methods, for example methods asdescribed in the Reference Examples or their obvious chemicalequivalents.

Aryl boronates of formula (XVII) wherein R¹, R², P² and P³ are ashereinbefore defined may be prepared by reaction of compounds of formula(XVIII) wherein R¹, R², P² and P³ are as hereinbefore defined, withbis(pinacolato)boron in the presence of potassium acetate and[1,1′-bis-(diphenylphosphino)ferroceno]-dichloropalladium (II) in aninert solvent, such as dioxane, at and at a temperature at about 80° C.

Compounds of formula (XVIII) wherein R¹ and R² are as hereinbeforedefined and P² and P³ are both tertiary-butoxycarbonyl may be preparedby reaction of compounds of formula (XXIX):

wherein R¹ and R² are as hereinbefore defined with sodium hydride anddi-tertiary-butyliminodicarboxylate, in an inert solvent, such astetrahydrofuran, and at a temperature at about room temperature.

Intermediates of formulae (VIII) and (XV) are novel compounds and, assuch, they and their processes described herein for their preparationconstitute further features of the present invention.

The present invention is further Exemplified but not limited by thefollowing illustrative Examples and Reference Examples.

In the nuclear magnetic resonance spectra (NMR) the chemical shifts areexpressed in ppm relative to tetramethylsilane. Abbreviations have thefollowing significances: br=broad, dd=double doublet, s=singlet;m=multiplet.

High Pressure Liquid Chromatography/Mass Spectrometry (LC-MS) conditionsfor determination of retention times (RT) were as follows: 3 micron LunaC18 (2) HPLC column (30 mm×4.6 mm) eluting with (i) mixture of 0.05%trifluoroacetic acid in acetonitrile and 0.05% trifluoroacetic acid inwater (1:19, v/v) for 2 minutes, (ii) mixture of 0.05% trifluoroaceticacid in acetonitrile and 0.05% trifluoroacetic acid in water (1:19 to19:1, v/v) gradient elution over 10 minutes, (iii) mixture of 0.05%trifluoroacetic acid in acetonitrile and 0.05% trifluoroacetic acid inwater (19:1, v/v) for 2 minutes, (iv) mixture of 0.05% trifluoroaceticacid in acetonitrile and 0.05% trifluoroacetic acid in water (1:19 to1:19, v/v) gradient elution over 2 minutes; flow rate 2ml/minute withapproximately 200 μl/minute split to the Mass Spectrometer; injectionvolume 10-40t; in line Diode Array (220-450 nm), in line Evaporativelight scattering (ELS) detection ELS—temperature 50° C., Gain 8—1.8ml/minute; Source temperature 150° C.

The present invention may be better understood by reference to thefollowing non-limiting Examples, which are provided as exemplary of theinvention. The following examples are presented in order to more fullyillustrate particular embodiments of the invention. They should in noway be construed, however, as limiting the broad scope of the invention.

In the nuclear magnetic resonance spectra (NMR), reported infra, thechemical shifts are expressed in ppm relative to tetramethylsilane.Abbreviations have the following significances: br=broad, dd=doubledoublet, s=singlet; m=multiplet.

Moreover, in the Examples, High Pressure Liquid Chromatography/MassSpectrometry (LC-MS) conditions for determination of retention times(RT) were as follows: 3 micron Luna C18 (2) HPLC column (30 mm×4.6 mm)eluting with (i) mixture of 0.05% trifluoroacetic acid in acetonitrileand 0.05% trifluoroacetic acid in water (1:19, v/v) for 2 minutes, (ii)mixture of 0.05% trifluoroacetic acid in acetonitrile and 0.05%trifluoroacetic acid in water (1:19 to 19:1, v/v) gradient elution over10 minutes, (iii) mixture of 0.05% trifluoroacetic acid in acetonitrileand 0.05% trifluoroacetic acid in water (19:1, v/v) for 2 minutes, (iv)mixture of 0.05% trifluoroacetic acid in acetonitrile and 0.05%trifluoroacetic acid in water (1:19 to 1:19, v/v) gradient elution over2 minutes; flow rate 2 ml/minute with approximately 200 μl/minute splitto the Mass Spectrometer; injection volume 10-40 μl; in line Diode Array(220-450 nm), in line Evaporative light scattering (ELS) detectionELS—temperature 50° C., Gain 8—1.8 ml/minute; Source temperature 150° C.

EXAMPLE 13-[1-(5-phenylethynyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylaminedi-hydrochloride

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(5-phenylethynyl-pyridin-3-yl)-methanone)dihydrochloride)

A.B-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-pinacolato-boron

A solution of 3-bromobenzylbromide (7.5 g, 30 mmol) anddi-tert-butyliminodicarboxylate (6.5 g, 30 mmol) in anhydroustetrahydrofuran (80 ml) was treated portionwise with sodium hydride (1.2g, 60% dispersion in mineral oil). After stirring at ambient temperaturefor 7 hours the reaction mixture was partitioned between saturatedaqueous ammonium chloride solution (90 ml) and ethyl acetate (2 lots of250 ml). The combined organic layers were washed with brine (75 ml),then dried over magnesium sulfate and then concentrated under vacuum.The residue was subjected to chromatography on silica gel eluting with amixture of pentane and dichloromethane (2:1, v/v) to give3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-bromobenzene as a paleyellow oil (9.52 g). A sample of this material (2.0 g, 5.2 mmol) wasdissolved in anhydrous dimethylsulfoxide (30ml) and the solution wastreated with potassium acetate (1.52 g, 15.5 mmol),bis(pinacolato)diboron (1.45 g, 5.7 mmol), and[1,1′-bis-(diphenylphosphino)ferroceno]-dichloropalladium(II)-dichloromethane complex (0.13 g, 0.16 mmol). This mixture wasstirred at 80° C. under an atmosphere of nitrogen for 5 hours, thencooled and then partitioned between water (100 ml) and diethyl ether (4lots of 75 ml). The combined organic layers were washed twice with brine(75 ml), then dried over magnesium sulfate and then concentrated undervacuum. The residue was subjected to chromatography on silica geleluting with a mixture of pentane and dichloromethane (2:1, v/v) to giveB-{3-[N,N-bis-(tert-butoxycarbonyl)-aminomethyl]-phenyl}-pinacolato-boronas a colorless oil (1.08 g). ¹H NMR (CDCl₃, 500 MHz): δ7.78 (s, 1H),7.70 (m, 1H), 7.39 (m, 1H), 7.30 (m, 1H), 4.79 (s, 2H), 1.27 (s, 18H),1.35 (s, 12H). MS(EI): 434(M⁺+H).

B. 4-{3-[N,N-Bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidine

A solution of lithium diisopropylamine (54 mmol) in anhydroustetrahydrofuran (50 ml), at −78° C., was treated dropwise with asolution of benzyl 4-oxo-1-piperidinecarboxylate (11.4 g, 49 mmol) inanhydrous tetrahydrofuran (50 ml). This mixture was stirred at −78° C.for 20 minutes and then treated with a solution ofN-phenyltrifluoromethanesulfonimide (19.26 g, 54 mmol) in anhydroustetrahydrofuran (55 ml). The resultant orange suspension was warmed to0° C., then stirred at 0° C. for 2 hours and then concentrated undervacuum. The residue was subjected to chromatography on silica geleluting with dichloromethane to yield benzyl1,2,3,6-tetrahydro-4-(trifluoromethylsulphonyloxy)-pyridine-1-carboxylateas a yellow oil (11.34 g). A portion of this material (0.84 g, 2.3 mmol)was dissolved in anhydrous dimethylformamide (20 ml) and the solutionwas treated withB-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl-pinacolato-boron(1.0 g, 2.3 mmol), potassium carbonate (0.96 g, 6.7 mmol) and[1,1′-bis-(diphenylphosphino)ferroceno]dichloropalladium(II)-dichloromethane complex (0.1 g, 0.14 mmol). This mixture was heatedat 80° C. under an atmosphere of nitrogen for 18 hours, then cooled andthen concentrated under vacuum. The residue was partitioned betweenethyl acetate (2 lots of 100 ml) and water (100 ml) containingconcentrated ammonium hydroxide (6 ml). The combined organic extractswere dried over magnesium sulfate and then concentrated under vacuum.The resultant oil was subjected to chromatography on silica gel elutingwith a mixture of ethyl acetate and pentane (1:4, v/v) to yield a yellowoil (0.9 g). This material was dissolved in ethanol (20 ml) and thesolution was treated with 10% palladium on carbon (20 mg) then stirredat ambient temperature under an atmosphere of hydrogen for 5 hours. Thereaction mixture was filtered through a short pad of hyflo and thefiltrate was concentrated under vacuum to give4-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidine ascolorless oil (0.54 g). 1H NMR (CDCl₃, 500 MHz): δ7.10 (m, 4H), 4.80 (s,2H), 4.45 (br m,1H), 3.20 (br m, 1H), 2.98 (br m, 1H), 2.75 (br m, 1H),1.90 (m, 1H), 1.75-1.60 (m, 3H), 1.42 (s, 18H). MS(EI): 391(M⁺+H).

C.N,N-Bis-(tert-butoxycarbonyl)-3-[1-(5-phenylethynyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamine

A solution of 5-phenylethynyl-pyridine-3-carboxylic acid (0.25 g, 1.1mmol) in anhydrous dimethylformamide (5 ml) was treated withO-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate (0.42 g, 1.1 mmol) and diisopropylethylamine (0.5ml, 3 mmol). This mixture was stirred 15 minutes at ambient temperatureand then treated with a solution of4-{3-[N,N-Bis-(tert-butoxycarbonyl)aminomethyl]-phenyl)-piperidine (0.39g, 1.0 mmol) in dimethylformamide (5 ml). After stirring at ambienttemperature for 18 hours the reaction mixture was concentrated undervacuum. The residue was partitioned between ethyl acetate (50 ml) andsaturated aqueous sodium bicarbonate (15 ml). The organic layer wasdried over magnesium sulfate and then concentrated under vacuum. Theresidue was subjected to chromatography on silica gel eluting with amixture of dichloromethane and methanol (49:1, v/v) to giveN,N-bis-(tert-butoxycarbonyl)-3-[1-(5-phenylethynyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamineas a yellow oil (0.25 g). ¹H NMR [(CD₃)₂SO, 500 MHz]: δ8.82 (s, 1H),8.62 (s, 1H), 8.02 (s, 1H), 7.61 (m, 2H), 7.45 (m, 3H), 7.30 (m, 1H),7.20 (m, 1H), 7.15 (m, 1H), 7.04 (m, 1H), 4.68 (s, 2H), 4.62 (br m, 1H),3.60 (br m, 1H), 3.23 (br m, 1H), 2.85 (m, 2H), 1.83 (br m, 1H), 1.65(m, 3H), 1.39 (s, 18H). MS(EI): 596(M⁺+H).

D.3-[1-(5-phenylethynyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylaminedi-hydrochloride

A solution of3-[1-(5-phenylethynyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzonitrile(0.15 g, 0.25 mmol) in ethyl acetate (20 ml) was cooled to 0° C. andthen saturated with hydrogen chloride gas. The reaction mixture wasstirred at ambient temperature for 4 hours and then concentrated todryness under vacuum. The residue was treated with ethyl acetate (10 ml)and the solvent removed under vacuum. This process was repeated twice togive3-[1-(5-phenylethynyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylaminedi-hydrochloride as a white solid (0.11 g). ¹H NMR [(CD₃)₂SO, 500 MHz]:δ8.83 (s, 1H), 8.63 (s, 1H), 8.08 (s, 1H), 7.61 (m, 2H), 7.45 (m, 3H),7.44 (s, 1H), 7.37 (m, 3H), 4.64 (br m, 1H), 4.00 (m, 2H), 3.62 (br m,1H), 3.25 (br m, 1H), 2.90 (br m, 2H), 1.88 (br m, 1H), 1.70 (m, 3H).MS(EI): 396(M⁺+H).

EXAMPLE 23-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl-benzylaminedi-hydrochloride

(A.K.A.[4-(3-aminomethyl-2-phenyl)-piperidin-1-yl]-(5-phenethyl-pyridin-3-yl)-methanonedi-hydrochloride)

A. 5-phenylethyl-pyridine-3-carboxylic acid

A solution of 5-phenylethynyl-pyridine-3-carboxylic acid (2 g, 8.9 mmol)in tetrahydrofuran (50 ml) was treated with 10% palladium on carbon (200mg) and stirred at ambient temperature under an atmosphere of hydrogenfor 5 hours. The reaction mixture was filtered through a short pad ofhyflo and the filtrate was concentrated under vacuum to give5-phenylethyl-pyridine-3-carboxylic acid as white solid (2 g). ¹H NMR[(CD₃)₂SO, 500 MHz]: δ8.90 (m, 1H), 8.60 (m, 1H), 8.12 (m, 1H), 7.21 (m,5H), 3.38 (br s, 1H), 2.95 (m, 4H).

B.N,N-Bis-(tert-butoxycarbonyl)-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamine

By proceeding in a similar manner to the method described in EXAMPLE 1C,but using of 5-phenylethyl-pyridine-3-carboxylic acid in place of5-phenylethynyl-pyridine-3-carboxylic acid, there was preparedN,N-bis-(tert-butoxycarbonyl)-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamineas a white amorphous solid. ¹H NMR [(CD₃)₂SO, 500 MHz]: δ8.50 (s, 1H),8.41 (s, 1H), 7.61 (m, 1H), 7.30-7.05 (m, 9H), 4.68 (s, 2H), 4.62 (br m,1H), 3.48 (br m, 1H), 3.35 (s, 4H), 3.18 (br m, 1H), 2.85 (m, 2H), 1.82(br m, 1H), 1.65 (br m, 1H), 1.58 (br m, 2H), 1.39 (s, 18H). MS(EI):600(M⁺+H).

C. 3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylaminedi-hydrochloride

By proceeding in a similar manner to the method described in EXAMPLE 1D,but usingN,N-bis-(tert-butoxycarbonyl)-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylaminein place ofN,N-Bis-(tert-butoxycarbonyl)-3-[1-(5-phenylethynyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamine,there was prepared3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylaminedi-hydrochloride as a white solid. ¹H NMR [(CD₃)₂SO, 500 MHz]: δ8.90 (m,2H), 8.42 (s, 1H), 7.58 (m, 1H), 7.38-7.20 (m, 8H), 4.62 (br m, 1H),4.00 (m, 2H), 3.45 (br m, 1H), 3.20 (br m, 1H), 3.17 (m, 2H), 3.00 (m,2H), 2.90 (br m, 2H), 1.88 (br m, 1H), 1.70 (br m, 3H). MS(EI):400(M⁺+H).

EXAMPLE 33-[1-(1-oxy-5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylaminehydrochloride

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(1-oxy-5-phenethyl-pyridin-3-yl)-methanonehydrochloride)

A solution ofN,N-Bis-(tert-butoxycarbonyl)-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamine(100 mg, 0.17 mmol, EXAMPLE 2B) in dichloromethane (10 ml) was treatedwith meta-chloroperbenzoic acid (80%, 80 mg, 0.37 mmol). After stirringfor 18 hours at ambient temperature the reaction mixture was dilutedwith dichloromethane (40 ml) and then washed three times with saturatedaqueous sodium bicarbonate solution (20 ml). The organic phase was driedover magnesium sulfate and then concentrated under vacuum. The residuewas subjected to chromatography on silica gel eluting with a mixture ofdichloromethane and methanol (98:2, v/v) to giveN,N-bis-(tert-butoxycarbonyl)-3-[1-(1-oxy-5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamineas a colorless oil (70 mg). This material was dissolved in ethyl acetate(10 ml) and the solution was cooled to 0° C., then saturated withhydrogen chloride gas, then stirred at ambient temperature for 4 hoursand then concentrated to dryness under vacuum. The residue was treatedwith ethyl acetate (10 ml) and the solvent removed under vacuum. Thisprocess was repeated twice to leave the title compound as a white solid(45 mg). ¹H NMR [(CD₃)₂SO, 500 MHz]: δ8.39 (s, 1H), 8.30 (s, 1H), 7.45(s, 1H), 7.40 (s, 1H), 7.38-7.18 (m, 8H), 4.59 (br m, 1H), 4.00 (m, 2H),3.50 (br m, 1H), 3.20 (br m, 1H), 2.98 (s, 4H), 2.85 (br m, 2H), 1.84(br m, 1H), 1.68 (br m, 3H). MS(EI): 416(M⁺+H).

EXAMPLE 4 3-[1-(quinoline-3-carbonyl)-piperidin-4-yl]-benzylaminedi-hydrochloride

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-quinolin-3-yl-methanonedi-hydrochloride) By proceeding in a similar manner to the methoddescribed in EXAMPLE 1, but using quinoline-3-carboxylic acid in placeof 5-phenylethynyl-pyridine-3-carboxylic acid, there was prepared thetitle compound as a white amorphous solid. ¹H NMR [(CD₃)₂SO, 500 MHz]:δ9.10 (s, 1H), 8.78 (s, 1H), 8.20 (m, 2H), 7.98 (m, 1H), 7.80 (m, 1H),7.50 (s, 1H), 7.35 (m, 3H), 4.72 (br m, 1H), 4.00 (m, 2H), 3.80 (br m,1H),3.30 (br m, 1H), 2.90 (br m,2H),1.90 (br m, 1H),1.75 (br m, 3H).MS(EI): 346(M⁺+H).

EXAMPLE 5 3-[1-(3-phenylethynyl-benzoyl)-piperidin-4-yl]-benzylaminehydrochloride

(A.K.A.[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-(3-phenylethynyl-phenyl)-methanonehydrochloride)

A.N,N-Bis-(tert-butoxycarbonyl)-3-[1-(3-ethynyl-benzoyl)-piperidin-4-yl]-benzylamine

By proceeding in a similar manner to the method described in EXAMPLE 1C,but using of 3-ethynyl-benzoic acid [prepared according to the proceduredescribed by C. Eaborn et al., J. Chem. Soc. C, 1967, (15), pages1364-1366] in place of 5-phenylethynyl-pyridine-3-carboxylic acid, therewas preparedN,N-bis-(tert-butoxycarbonyl)-3-[1-(3-ethynyl-benzoyl)-piperidin-4-yl]-benzylamineas a white amorphous solid. ¹H NMR (CDCl₃, 500 MHz): δ7.76 (m, 2H), 7.40(m, 2H), 7.25 (m, 2H), 7.10 (m, 4H), 4.95 (br m,1H), 4.79 (s, 2H), 3.80(br m, 1H), 3.10 (br m, 1H), 2.84 (br m, 1H), 2.78 (br m, 1H), 1.90 (m,1H), 1.75 (m, 3H), 1.42 (s, 18H). MS(EI): 541(M⁺+Na).

B.N,N-Bis-(tert-butoxycarbonyl)-3-[1-(3-phenylethynyl-benzoyl)-]piperidin-4-yl]-benzylamine

A mixture ofN,N-bis-(tert-butoxycarbonyl)-3-[1-(3-ethynyl-benzoyl)-piperidin-4-yl]-benzylamine(0.24 g, 0.46 mmol), iodobenzene (95 mg, 0.46 mmol),dichlorobis(triphenylphosphine)palladium (II) (35 mg, 0.05 mmol), copper(I) iodide (26 mg, 0.14 mmol), triethylamine (0.57 ml, 4.1 mmol) andanhydrous dimethylformamide (8 ml) was stirred at ambient temperatureunder nitrogen for 18 hours. The solvent was removed under vacuum andthe residue was partitioned between ethyl acetate (3 lots of 50 ml) andwater (20 ml). The combined organic layers were washed with brine (50ml), then dried over magnesium sulfate and then concentrated undervacuum. The residue was subjected to chromatography on silica geleluting with a mixture of cyclohexane and ethyl acetate (3:2, v/v) togiveN,N-bis-(tert-butoxycarbonyl)-3-[1-(3-phenylethynyl-benzoyl)-piperidin-4-yl]-benzylamineas a yellow oil (0.23 g). ¹H NMR (CDCl₃, 500 MHz): δ7.58 (m, 4H), 7.40(m,5H), 7.25 (m, 1H), 7.10 (m, 3H), 4.90 (br m,1H), 4.79 (s, 2H), 3.80(br m, 1H), 3.15 (br m, 1H), 2.84 (br m, 1H), 2.78 (br m, 1H), 1.95 (m,1H), 1.80 (m, 3H), 1.42 (s, 18H). MS(EI): 617(M⁺+Na).

C. 3-[1-(3-phenylethynyl-benzoyl)-piperidin-4-yl]-benzylaminehydrochloride

A solution ofN,N-Bis-(tert-butoxycarbonyl)-3-[1-(3-phenylethynyl-benzoyl)-piperidin-4-yl]-benzylamine(100 mg, 0.17 mmol) in methanol (10 ml), cooled to 0° C., was saturatedwith hydrogen chloride gas. The mixture was stirred at ambienttemperature for 4 hours then concentrated to dryness under vacuum. Theresidue was triturated with a mixture of dichloromethane and diethylether to give 3-[1-(3-phenylethynyl-benzoyl)-piperidin-4-yl]-benzylaminehydrochloride as a white amorphous solid (46 mg). ¹H NMR [(CD₃)₂SO, 500MHz]: δ7.61-7.30 (m, 13H), 4.62 (br m, 1H), 4.00 (s, 2H), 3.62 (br m,1H), 3.25 (br m, 1H), 2.85 (br m, 2H), 1.88 (br m, 1H), 1.70 (br m, 3H).MS(EI): 395(M⁺+H).

EXAMPLE 62-{3-[4-(3-aminomethyl-phenyl)-piperidine-1-carbonyl]-phenyl}-1-(4-hydroxyphenyl)-ethanone

(A.K.A.2-{3-[4-(3-aminomethyl-phenyl)-piperidine-1-carbonyl]-phenyl}-1-(4-hydroxy-phenyl)-ethanonehydrochloride)

A.N,N-Bis-(tert-butoxycarbonyl)-3-{1-[3-(4-hydroxyphenyl)ethynyl-benzoyl]-piperidin-4-yl}-benzylamine

By proceeding in a similar manner to the method described in EXAMPLE 5B,but using 4-iodophenol in place of iodobenzene, there was preparedN,N-bis-(tert-butoxycarbonyl)-3-{1-[3-(4-hydroxyphenyl)ethynyl-benzoyl]-piperidin-4-yl}-benzylamineas a yellow amorphous solid. ¹H NMR (CDCl₃, 500 MHz): δ7.58 (m, 2H),7.40 (m, 4H), 7.25 (m, 1H), 7.15 (m, 3H), 6.80 (m, 2H), 4.90 (br m,1H),4.79 (s, 2H), 3.90 (br m, 1H), 3.15 (br m, 1H), 2.84 (br m, 1H), 2.78(br m, 1H), 1.98 (m, 1H), 1.80 (m, 3H), 1.42 (s, 18H). MS(EI):633(M⁺+Na).

B.2-3-[4-(3-aminomethyl-phenyl)-piperidine-1-carbonyl]-phenyl}-1-(4-hydroxyphenyl)-ethanonehydrochloride

By proceeding in a similar manner to the method described in EXAMPLE 5Cbut usingN,N-bis-(tert-butoxycarbonyl)-3-{1-[3-(4-hydroxyphenyl)ethynyl-benzoyl]-piperidin-4-yl}-benzylamine,there was prepared2-{3-[4-(3-aminomethyl-phenyl)-piperidine-1-carbonyl]-phenyl}-1-(4-hydroxyphenyl)-ethanonehydrochloride as a white amorphous solid. ¹H NMR [(CD₃)₂SO, 500 MHz]:δ7.92 (m, 2H), 7.40-7.28 (m, 8H), 6.82 (m, 2H), 4.60 (br m, 1H), 4.38(s, 2H), 4.00 (s, 2H), 3.62 (br m, 1H), 3.18 (br m, 1H), 2.80 (br m,2H), 1.88 (br m, 1H), 1.70-1.60 (br m, 3H), MS(EI): 429(M⁺+H).

EXAMPLE 73-{1-[3-(6-amino-pyridin-3-yl)ethynyl-benzoyl]-piperidin-4-yl}-benzylaminehydrochloride

(A.K.A.[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-[3-(6-amino-pyridin-3-ylethynyl)-phenyl]-methanonehydrochloride)

A. 3-Iodo-6-(tert-butoxycarbonylamino)pyridine

A stirred solution of 6-amino-3-iodopyridine (0.44 g, 2.0 mmol) inanhydrous tetrahydrofuran (7 ml), under nitrogen, was treated dropwisewith a solution of sodium bis(trimethylsilyl)amide (1M, 4.4 ml, 4.4mmol). After stirring for a further 15 minutes the mixture was treatedwith a solution of di-tert-butyldicarboxylate (440 mg, 2 mmol) inanhydrous tetrahydrofuran (3 ml). The resulting thick slurry was stirredat ambient temperature for 18 hours then partitioned between ethylacetate (3 lots of 50 ml) and water (50 ml). The combined organics weredried over sodium sulfate then concentrated under vacuum. The residuewas subjected to chromatography on silica gel eluting with a mixture ofcyclohexane and ethyl acetate (9:1, v/v) to give3-iodo-6-(tert-butoxycarbonylamino)pyridine as a white solid (0.56 g).¹H NMR (CDCl₃, 500 MHz) δ8.50 (s, 1H), 7.92 (m, 1H), 7.85 (m, 1H), 1.58(s, 9H). MS(EI): 319(M⁺−H).

B.N,N-Bis-(tert-butoxycarbonyl)-3-{1-[3-(6-tert-butoxycarbonylamino-pyridin-3-yl)ethynyl-benzoyl]-piperidin-4-yl}-benzylamine

By proceeding in a similar manner to the method described in EXAMPLE 5B,but using 3-iodo-6-(tert-butoxycarbonylamino)pyridine in place ofiodobenzene, there was preparedN,N-bis-(tert-butoxycarbonyl)-3-{1-[3-(6-tert-butoxycarbonylamino-pyridin-3-yl)ethynyl-benzoyl]-piperidin-4-yl}-benzylamineas a yellow amorphous solid. ¹H NMR (CDCl₃, 500 MHz): δ8.41 (s, 1H),7.99 (m, 1H), 7.80 (m, 1H), 7.61 (s, 1H), 7.59 (m, 2H), 7.40 (m, 2H),7.23 (m, 1H), 7.12 (m, 3H), 4.90 (br m,1H), 4.79 (s, 2H), 3.84 (br m,1H), 3.15 (br m, 1H), 2.84 (br m, 1H), 2.78 (br m, 1H), 1.95 (m, 1H),1.80 (m, 3H), 1.55 (s, 9H), 1.42 (s, 18H). MS(EI): 710(M⁺).

C.3-{1-[3-(6-amino-pyridin-3-yl)ethynyl-benzoyl]-piperidin-4-yl}-benzylaminehydrochloride

By proceeding in a similar manner to the method described in EXAMPLE 5Cbut usingN,N-bis-(tert-butoxycarbonyl)-3-{1-[3-(6-tert-butoxycarbonylamino-pyridin-3-yl)ethynyl-benzoyl]-piperidin-4-yl}-benzylamine,there was prepared3-{1-[3-(6-Amino-pyridin-3-yl)ethynyl-benzoyl]-piperidin-4-yl}-benzylaminehydrochloride as a white amorphous solid. ). ¹H NMR [(CD₃)₂SO, 500 MHz]:δ8.22 (s, 1H), 8.15 (br s, 2H), 7.90 (m, 1H), 7.60-7.41 (m, 5H), 7.30(m, 3H), 6.93 (m, 1H), 4.60 (br m, 1H), 4.00 (m, 2H), 3.62 (br m, 1H),3.25 (br m, 1H), 2.85 (br m, 2H), 1.84 (br m, 1H), 1.60 (br m, 3H).MS(EI): 41 1(M⁺+H).

EXAMPLE 83-{1-[3-(4-hydroxymethylphenyl)ethynyl-benzoyl]-piperidin-4-yl}-benzylaminehydrochloride

(A.K.A.[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-[3-(4-hydroxymethyl-phenylethynyl)-phenyl]-methanonehydrochloride)

By proceeding in a similar manner to the method described in EXAMPLE 5,but using 4-iodobenzylalcohol (prepared according to the proceduredescribed by D. S. Tan et al., J. Am. Chem. Soc., 1998, 120(33), pages8565-8566) in place of iodobenzene, there was prepared the titlecompound as a white amorphous solid. ¹H NMR [(CD₃)₂SO, 500 MHz]:δ7.61-7.25 (m, 12H), 5.33 (m, 1H), 4.62 (br m, 1H), 4.58 (m, 2H), 4.00(s, 2H), 3.62 (br m, 1H), 3.20 (br m, 1H), 2.83 (br m, 2H), 1.84 (br m,1H), 1.72-1.62 (br m, 3H). MS(EI): 425(M⁺+H).

EXAMPLE 9 3-[1-(3-phenylethyl-benzoyl)-piperidin-4-yl]-benzylaminehydrochloride

(A.K.A.[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-(3-phenethyl-phenyl)-methanonehydrochloride)

A solution ofN,N-bis-(tert-butoxycarbonyl)-3-[1-(3-phenylethynyl-benzoyl)-piperidin-4-yl]-benzylamine(110 mg, 0.18 mmol, EXAMPLE 5B) in ethanol (10 ml) was treated with 10%palladium on carbon (20 mg) and then stirred at ambient temperatureunder an atmosphere of hydrogen for 8 hours. The reaction mixture wasfiltered through a short pad of hyflo and then concentrated under vacuumto give a white amorphous solid (0.54 g). This material was treated withmethanolic hydrogen chloride according to the procedure described inEXAMPLE 5C to give the title compound as white amorphous solid (25 mg).¹H NMR [(CD₃)₂SO, 500 MHz]: δ7.40-7.15 (m, 13H), 4.62 (br m, 1H), 4.00(s, 2H), 3.60 (br m, 1H), 3.10 (br m, 1H), 2.80 (br m, 2H), 1.85 (br m,1H), 1.60 (br m, 3H), MS(EI): 399(M⁺+H).

EXAMPLE 103-{1-[3-(4-hydroxyphenyl)ethyl-benzoyl]-piperidin-4-yl}-benzylaminehydrochloride

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-{3-[2-(4-hydroxy-phenyl)-ethyl]-phenyl}-methanonehydrochloride)

By proceeding in a similar manner to the method described in EXAMPLE 9,but usingN,N-bis-(tert-butoxycarbonyl)-3-{1-[3-(4-hydroxyphenyl)ethynyl-benzoyl]-piperidin-4-yl}-benzylamine (EXAMPLE 6A), there was prepared the title compound as a whiteamorphous solid. ¹H NMR [(CD₃)₂SO, 500 MHz]: δ9.18 (br s, 1H), 7.41 (s,1H), 7.35 (m, 5H), 7.20 (m, 2H), 6.98 (m, 2H), 6.60 (m, 2H), 4.82 (brm,1H), 4.00 (m, 2H), 3.80 (br m, 1H), 3.10 (br m, 1H), 2.80 (m, 6H),1.82 (br m, 1H), 1.70 (br m, 1H), 1.60 (br m, 2H). MS(EI): 415(M⁺+H).

EXAMPLE 113-{1-[3-(6-amino-pyridin-3-yl)ethyl-benzoyl]-piperidin-4-yl}-benzylaminehydrochloride

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-{3-[2-(6-amino-pyridin-3-yl)-ethyl]-phenyl}-methanonehydrochloride)

By proceeding in a similar manner to the method described in EXAMPLE 9,but usingN,N-bis-(tert-butoxycarbonyl)-3-{1-[3-(6-tert-butoxycarbonylamino-pyridin-3-yl)ethynyl-benzoyl]-piperidin-4-yl}-benzylamine(EXAMPLE 7B), there was prepared the title compound as a white amorphoussolid. 1H NMR [(CD₃)₂SO, 500 MHz]: δ7.90 (br s, 2H), 7.85 (m, 1H), 7.76(s, 1H), 7.43 (s, 1H), 7.40-7.30 (m, 5H), 7.24 (m, 2H), 6.93 (m, 1H),4.61 (br m, 1H), 4.00 (m, 2H), 3.60 (br m, 1H), 3.15 (br m, 1H), 2.92(br m, 6H), 1.90 (br m, 1H), 1.70 (br m, 1H), 1.60 (br m, 2H). MS(EI):415(M⁺+H).

EXAMPLE 123-[1(4-phenylethyl-thiophene-2-carbonyl)-piperidin-4-yl]-benzylaminehydrochloride

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(4-phenethyl-thiophen-2-yl)-methanonehydrochloride)

By proceeding in a similar manner to the method described in EXAMPLE 1,but using 4-phenylethyl-thiophene-2-carboxylic acid (prepared accordingthe procedure described by S.Gronowitz et al., Heterocycles, 1981,15(2), pages 947-959) in place of 5-phenylethynyl-pyridine-3-carboxylicacid, there was prepared the title compound as a white amorphous solid.¹H NMR [(CD₃)₂SO, 500 MHz]: δ7.41-7.18 (m, 11H), 4.37 (br m, 1H), 4.00(m, 2H), 3.05 (br m, 2H), 2.98 (s, 4H), 2.85 (br m, 2H), 1.90 (br m,2H), 1.60 (br m, 2H), MS(EI): 405(M⁺+H).

EXAMPLE 133-[1-(5-phenylethyl-thiophene-2-carbonyl)-piperidin-4-yl]-benzylaminehydrochloride

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(5-phenethyl-thiophen-2-yl)-methanonehydrochloride)

By proceeding in a similar manner to the method described in EXAMPLE 2,but using 5-phenylethynyl-thiophene-2-carboxylic acid in place of5-phenylethynyl-pyridine-3-carboxylic acid, there was prepared the titlecompound as a white amorphous solid. ¹H NMR [(CD₃)₂SO, 500 MHz]: δ7.41(s, 1H), 7.38-7.20 (m, 9H), 6.83 (s, 1H), 4.40 (br m, 1H), 4.00 (br s,2H), 3.12 (m, 2H), 3.08 (br m, 2H), 2.98 (m, 2H), 2.85 (br m, 2H), 1.82(br m, 2H), 1.60 (br m, 2H), MS(EI): 405(M⁺+H).

EXAMPLE 143-{1-[3-(benzooxazo-2-yl)-benzoyl]-piperidin-4-yl}-benzylaminehydrochloride

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(3-benzoxazol-2-yl-phenyl)-methanonehydrochloride)

By proceeding in a similar manner to the method described in EXAMPLE 1,but using 3-(benzooxazo-2-yl)-benzoic acid (prepared according to theprocedure described by V. F. Bystrov et al., Zh. Obshch. Khim., 1968,38(5), pages 1001-1005) in place of5-phenylethynyl-pyridine-3-carboxylic acid, there was prepared the titlecompound as a white amorphous solid. ¹H NMR [(CD₃)₂SO, 500 MHz]: δ8.28(m, 1H), 8.19 (s, 1H), 7.81 (m, 2H), 7.50 (m, 2H), 7.43 (m, 3H), 7.30(m, 3H), 4.66 (br m, 1H), 4.00 (m, 2H), 3.70 (br m, 1H), 3.25 (br m,1H), 2.92 (br m, 1H), 2.82 (br m, 1H), 1.90 (br m, 1H), 1.70 (br m, 3H),MS(EI): 412(M⁺+H).

EXAMPLE 15 3-[1-(3-phenoxymethyl-benzoyl)-piperidin-4-yl]-benzylaminehydrochloride

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(3-phenoxymethyl-phenyl)-methanonehydrochloride)

By proceeding in a similar manner to the method described in EXAMPLE 1,but using 3-phenoxymethyl-benzoic acid (prepared according to theprocedure of H.Oelschlaeger et al., Arch. Pharm. (Weinheim, Ger.), 1978,311(2), pages 81-97) in place of 5-phenylethynyl-pyridine-3-carboxylicacid, there was prepared the title compound as a white amorphous solid.¹H NMR [(CD₃)₂SO, 500 MHz]: δ7.58-7.25 (m, 10H), 7.00 (m, 2H), 6.96 (m,1H), 5.18 (s, 2H), 4.62 (br m, 1H), 4.00 (m, 2H), 3.62 (br m, 1H), 3.18(br m, 1H), 2.82 (br m, 2H), 1.88 (br m, 1H), 1.65 (br m, 3H), MS(EI):401(M⁺+H).

EXAMPLE 163-{1-[3-(2-E-phenylethenyl)-benzoyl]-piperidin-4-yl}-benzylaminehydrochloride

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-[3-((E)-styryl)-phenyl]-methanonehydrochloride)

By proceeding in a similar manner to the method described in EXAMPLE 1,but using 3-(2-E-phenylethenyl)-benzoic acid (prepared according to theprocedure of N. A. Bumagin et al., Zh. Org. Khim., 1995, 31(4), pages481-487) in place of 5-phenylethynyl-pyridine-3-carboxylic acid, therewas prepared the title compound as a white amorphous solid. ¹H NMR[(CD₃)₂SO, 500 MHz]: δ7.71 (m, 1H), 7.63 (m, 3H), 7.50 (m, 2H),7.40-7.25 (m, 9H), 4.63 (br m, 1H), 4.00 (s, 2H), 3.71 (br m, 1H), 3.10(br m, 1H), 2.84 (br m, 2H), 1.88 (br m, 1H), 1.70 (br m, 3H), MS(EI):397(M⁺+H).

EXAMPLE 174-Fluoro-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylaminedi-hydrochloride

(A.K.A.[4-(5-Aminomethyl-2-fluoro-phenyl)-piperidin-1-yl]-(5-phenethyl-pyridin-3-yl)-methanonedi-hydrochloride)

A. 4-(Pinacolatoboronyl)-1,2,3,6-tetrahydro-pyridine trifluoroacetate

A solution of lithium diisopropylamine (59 mmol) in anhydroustetrahydrofuran (50 ml) at −78° C. was treated dropwise with a solutionof tert-butyl 4-oxo-1-piperidinecarboxylate (10.7 g, 54 mmol) inanhydrous tetrahydrofuran (70 ml). After stirring at −78° C. for afurther 20 minutes the reaction mixture was treated with a solution ofN-phenyltrifluoromethanesulfonimide (21.2 g, 59 mmol) in anhydroustetrahydrofuran (90 ml). The resultant orange suspension was warmed to0° C., then stirred at 0° C. for 3 hours and then concentrated undervacuum. The residue was subjected to chromatography on silica geleluting with a mixture of pentane and dichloromethane (1:1, v/v) andthen subjected to chromatography on alumina eluting with a mixture ofpentane and ethyl acetate (9:1, v/v) to yield tert-butyl1,2,3,6-tetrahydro-4-(trifluoromethylsulphonyloxy)-pyridine-1-carboxylateas a yellow oil (15 g). A portion of this material (1.72 g, 5.2 mmol)was dissolved in anhydrous dioxane (30 ml) and the solution was treatedwith bis(pinacolato)diboron (1.46 g, 5.75 mmol), potassium acetate (1.54g, 15.7 mmol), (diphenylphosphino)-ferrocene (86 mg, 0.16 mmol) and[1,1′-bis-(diphenylphosphino)ferroceno]-dichloropalladium (II) (114 mg,0.16 mmol). The reaction mixture was heated at 80° C. under anatmosphere of nitrogen for 18 hours, then cooled and then concentratedunder vacuum. The residue was partitioned between ethyl acetate (2 lotsof 100 ml) and water (100 ml). The combined organic extracts were driedover magnesium sulfate then concentrated under vacuum. The resultant oilwas subjected to chromatography on silica gel eluting with a mixture ofethyl acetate and pentane (1:8, v/v) to yield a yellow oil (1.4 g). Asolution of this material in dichloromethane (10 ml), cooled to 0° C.,was treated with trifluoracetic acid (3.9 ml). The mixture was stirredat ambient temperature for 2 hours then concentrated under vacuum toleave 4-(pinacolatoboronyl)-1,2,3,6-tetrahydro-pyridine trifluoroacetateas a brown oil. ¹H NMR [(CD₃)₂SO, 500 MHz]: δ8.76 (br s, 2H), 6.39 (brs, 1H), 3.61 (br m, 2H), 3.11 (br m, 2H), 2.23 (br m, 2H), 1.20 (s 12H).MS(EI): 210(M⁺+H).

B.1-(5-Phenylethyl-pyridine-3-carbonyl)-4-(pinacolatoboronyl)-1,2,3,6-tetrahydro-pyridine

A solution of 5-phenylethyl-pyridine-3-carboxylic acid (0.46 g, 2.0mmol, EXAMPLE 2A) in anhydrous dimethylformamide (9 ml) was treated withO-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate (0.87 g, 2.2 mmol) and diisopropylethylamine (1.7ml, 10 mmol). This mixture was stirred at ambient temperature for 10minutes then treated with a solution of4-(pinacolatoboronyl)-1,2,3,6-tetrahydro-pyridine trifluoroacetate (0.81g, 2.5 mmol) in dimethylformamide (9 ml). The reaction mixture wasstirred at ambient temperature for 18 hours and then concentrated undervacuum. The residue was partitioned between dichloromethane (2 lots of50 ml) and saturated aqueous sodium bicarbonate (15 ml). The combinedorganic layers were dried over magnesium sulfate and then concentratedunder vacuum. The residue was subjected to chromatography on silica geleluting with ethyl acetate to give1-(5-phenylethyl-pyridine-3-carbonyl)-4-(pinacolatoboronyl)-1,2,3,6-tetrahydro-pyridineas a brown amorphous solid (0.73 g). ¹H NMR [(CD₃)₂SO, 500 MHz]: δ8.49(s, 1H), 8.40 (s, 1H), 7.61 (s, 1H), 7.20 (m, 5H), 6.48 (br s, 1H), 4.18(br m, 1H), 3.83 (br m, 1H), 3.62 (br m, 1H), 3.23 (br m, 1H), 2.98 (m,4H), 2.17 (br m, 2H), 1.20 (s, 12H). MS(EI): 441(M⁺+Na).

C. N-(tert-Butoxycarbonyl)-3-bromo-4-fluoro-benzylamine

A mixture of 3-bromo-4 fluoro-benzylamine hydrochloride (2.41 g, 10mmol), triethylamine (2.8 ml, 20 mmol), and di-tert-butoxycarbonate (1.8g, 10.3 mmol) in dichloromethane (20 ml) was stirred at ambienttemperature for 18 hours then washed with water (20 ml). The organicphase was dried over magnesium sulfate and then concentrated undervacuum. The residue was subjected to chromatography on silica geleluting with a mixture of cyclohexane and ethyl acetate (3:1, v/v) togive N-(tert-butoxycarbonyl)-3-bromo-4-fluoro-benzylamine as a whitesolid (1.4 g). ¹H NMR (CDCl₃, 500 MHz): δ7.45 (m, 1H), 7.20 (m, 1H),7.08 (m, 1H), 4.85 (br s, 1H), 4.21 (m, 2H), 1.42 (s, 9H).

D.N-(tert-Butoxycarbonyl)-4-fluoro-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-1,2,3,6-tetrahydro-pyridin-4-yl]-benzylamine

A mixture of N-(tert-butoxycarbonyl)-3-bromo-4-fluoro-benzylamine (0.28g, 0.92 mmol), anhydrous dimethylformamide (10 ml),1-(5-phenylethyl-pyridine-3-carbonyl)-4-(pinacolatoboronyl)-1,2,3,6-tetrahydro-pyridine(0.37 g, 0.88 mmol), potassium carbonate (0.36 g, 2.6 mmol) and[1,1′-bis-(diphenylphosphino)ferroceno]dichloropalladium(II)-dichloromethane complex (43 mg, 0.05 mmol) was heated at 80° C.under an atmosphere of nitrogen for 18 hours. The reaction mixture wascooled to room temperature and then concentrated under vacuum. Theresidue was partitioned between ethyl acetate (2 lots of 50 ml) andwater (10 ml). The combined organic extracts were dried over magnesiumsulfate and then concentrated under vacuum. The resultant oil wassubjected to chromatography on silica gel eluting with ethyl acetate toyieldN-(tert-butoxycarbonyl)-4-fluoro-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-1,2,3,6-tetrahydro-pyridin-4-yl]-benzylamineas a pale yellow oil (0.18 g). ¹H NMR (CDCl₃, 500 MHz): δ8.58 (s, 1H),8.50 (s, 1H), 7.51 (s, 1H), 7.25 (m, 2H), 7.18 (m, 5H), 7.00 (m, 1H),6.01 (br s, 1H), 4.83 (br s, 1H), 4.38 (br m, 1H), 4.27 (m, 2H), 3.98(br m, 2H), 3.50 (br m, 1H), 2.99 (m, 4H), 2.60 (br m, 1H), 2.50 (br m,1H). MS(EI): 538(M⁺+Na).

E.4-Fluoro-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylaminedi-hydrochloride

A solution ofN-(tert-butoxycarbonyl)-4-fluoro-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-1,2,3,6-tetrahydro-pyridin-4-yl]-benzylaminein ethanol (12 ml) was treated with 10% palladium on carbon (75 mg) andthe mixture was stirred at ambient temperature under an atmosphere ofhydrogen for 72 hours. The reaction mixture was filtered through a shortpad of hyflo and the filtrate was concentrated under vacuum to giveN-(tert-butoxycarbonyl-4-fluoro-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamineas colorless oil (85 mg). This material was dissolved in methanol (10ml) and the solution was cooled to 0° C. and then saturated withhydrogen chloride gas. This mixture was stirred at ambient temperaturefor 4 hours and then concentrated to dryness under vacuum. The residuewas triturated with a mixture of dichloromethane and diethyl ether togive4-fluoro-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylaminedi-hydrochloride as a white amorphous solid (50 mg). ¹H NMR [(CD₃)₂SO,500 MHz]: δ8.60 (s, 1H), 8.58 (s, 1H), 7.83 (s, 1H), 7.60 (m, 1H), 7.38(m, 1H), 7.20 (m, 6H), 4.61 (br m, 1H), 4.00 (m, 2H), 3.50 (br m, 1H),3.20 (br m, 2H), 2.99 (m, 2H), 2.95 (m, 2H), 2.90 (br m, 1H), 1.82 (brm, 1H), 1.65 (br m, 3H). MS(EI): 418(M⁺+H).

EXAMPLE 184-methyl-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylaminedi-hydrochloride

(A.K.A.[4-(5-Aminomethyl-2-methyl-phenyl)-piperidin-1-yl]-(5-phenethyl-pyridin-3-yl)-methanonedi-hydrochloride)

A. 4-[N,N-Bis-(tert-butoxycarbonyl)aminomethyl]-2-bromo-toluene

A solution of 4-methyl-3-bromobenzylbromide (1.63 g, 6.2 mmol, preparedaccording to the procedure described in International Patent ApplicationNo. WO 0009475) and di-tert-butyliminodicarboxylate (1.48 g, 6.8 mmol)in anhydrous tetrahydrofuran (15 ml) was treated portionwise with sodiumhydride (0.27 g of 60% dispersion in mineral oil, 6.8 mmol). The mixturewas stirred at ambient temperature for 18 hours then partitioned betweensaturated aqueous ammonium chloride solution (20 ml) and ethyl acetate(3 lots of 80 ml). The combined organic layers were washed with brine(80 ml), then dried over magnesium sulfate and concentrated undervacuum. The residue was subjected to chromatography on silica geleluting with a mixture of cyclohexane and diethyl ether (9:1, v/v) togive 4-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-2-bromo-toluene as apale yellow oil (2.4 g). ¹H NMR (CDCl₃, 500 MHz): δ7.45 (s, 1H), 7.18(m, 2H), 4.71 (s, 2H), 2.38 (s, 3H), 1.43 (s, 18H).

B.4-Methyl-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylaminedi-hydrochloride

By proceeding in a similar manner to the method described in EXAMPLE 17,but using 4-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-2-bromo-toluenein place of N-(tert-butoxycarbonyl)-3-bromo-4-fluoro-benzylamine, therewas prepared4-methyl-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylaminedi-hydrochloride as a white amorphous solid. ¹H NMR [(CD₃)₂SO, 500 MHz]:δ8.60 (m, 2H), 7.83 (s, 1H), 7.41 (s, 1H), 7.20 (m, 7H), 4.62 (br m,1H), 3.98 (m, 2H), 3.45 (br m, 1H), 3.20 (br m, 1H), 3.07 (m, 2H), 3.00(m, 2H), 2.95 (m, 2H), 2.32 (s, 3H), 1.80 (br m, 1H), 1.70 (br m, 3H).MS(EI): 414(M⁺+H).

EXAMPLE 193-{1-[3-(5-phenyl-1,3,4-oxadiazol-2-yl)-phenylcarbonyl]-piperidin-4-yl}-benzylaminehydrochloride

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-[3-(5-phenyl-1,3,4-oxadiazol-2-yl)-phenyl]-methanonehydrochloride)

A. 3-(5-Phenyl-1,3,4-oxadiazol-2-yl)-benzoic acid

A mixture of methyl hydrogen isopthalalate (1.8 g, 10 mmol), benzoichydrazide (1.4 g, 10 mmol) and phosphorous oxychloride (20 ml), under anatmosphere of nitrogen, was heated at 120° C. for 18 hours, then cooledto room temperature and then poured into ice water (500 ml). Thismixture was treated with solid sodium carbonate until the aqueous layerwas basic (pH 8-9) and the resultant pink solid was filtered. Thismaterial was treated with 100 ml methanol and the suspension was treatedwith sodium hydroxide solution (30 ml, 1M). The reaction mixture washeated at reflux for 4 hours, then cooled and then concentrated todryness. The residue was dissolved in water (100 ml) and the solutionwas acidified to pH 3 by addition of concentrated hydrochloric acid. Theresultant precipitate was filtered, then dried and then subjected tochromatography on silica gel eluting with a mixture of dichloromethaneand methanol (98:2, v/v) to yield3-(5-phenyl-1,3,4-oxadiazol-2-yl)-benzoic acid as a white solid (600mg). ¹H NMR [(CD₃)₂SO, 500 MHz]: δ8.80 (s, 1H), 8.38 (m, 1H), 8.18 (m,3H), 7.78 (m, 1H), 7.62 (m, 3H). MS(EI): 265(M⁺−H).

B.3-{1-[3-(5-Phenyl-1,3,4-oxadiazol-2-yl)-phenylcarbonyl]-piperidin-4-yl}-benzylaminehydrochloride

By proceeding in a similar manner to the method described in EXAMPLE 1,but using 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-benzoic acid in place of5-phenylethynyl-pyridine-3-carboxylic acid, there was prepared3-{1-[3-(5-phenyl-1,3,4-oxadiazol-2-yl)-phenylcarbonyl]-piperidin-4-yl}-benzylaminehydrochloride as a pale yellow amorphous solid. ¹H NMR [(CD₃)₂SO, 500MHz]: δ8.21 (m, 1H), 8.20 (m, 3H), 7.75 (m, 2H), 7.68 (m, 3H), 7.50 (s,1H), 7.37 (m, 3H), 4.70 (br m, 1H), 4.00 (m, 2H), 3.70 (br m, 1H), 3.25(br m, 1H), 2.90 (br m, 1H), 2.85 (br m, 1H), 1.88 (br m, 1H), 1.70 (m,3H), MS(EI): 439(M⁺+H).

EXAMPLE 20 3-[1-(indole-6-carbonyl)-piperidin-4-yl]-benzylaminetrifluoroacetate

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(1H-indol-6-yl)-methanonetrifluoroacetate)

A solution of diisopropylamine in dimethylformamide (1 ml, 180M) in aglass vial was treated with a solution ofO-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate in dimethylformamide (1 ml, 60 μM) followed by asolution of indole-6-carboxylic acid in dimethylformamide (1 ml, 60,μM).After standing at ambient temperature for 15 minutes the mixture wastreated with a solution of4-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidine indimethylformamide (1 ml, 60 μM, EXAMPLE 1B). The reaction mixture wasallowed to stand at ambient temperature for 18 hours then evaporated.The residue was treated with chloroform (5 ml) and aqueous sodiumcarbonate solution (5%). This mixture was shaken gently for 30 minutes,poured into a fritted polypropylene tube and the organic layer whichpasses through the frit collected in a glass vial. The chloroform wasevaporated under vacuum and the residue was treated with a mixture oftrifluoroacetic acid, dichloromethane and water (4 ml, 55/40/5, v/v/v).This mixture was shaken gently for 2 hours and then evaporated to leavethe title compound as a yellow oil. LC-MS: R_(T)=3.43 minutes (>96% byELSD); MS (ES⁺), 334 (MH⁺).

EXAMPLE 21 3-[1-(coumarin-3-carbonyl)-piperidin-4-yl]-benzylaminetrifluoroacetate

(A.K.A.3-[4-(3-Aminomethyl-phenyl)-piperidine-1-carbonyl]-1-benzopyran-2-onetrifluoroacetate)

By proceeding in a similar manner to the method described in EXAMPLE 20,but using coumarin-3-carboxylic acid in place of indole-6-carboxylicacid, there was prepared the title compound as a yellow oil. LC-MS:R_(T)=3.15 minutes (>86% by ELSD); MS (ES⁺), 363 (MH⁺).

EXAMPLE 22 3-[1-(naphthyl-2-carbonyl)-piperidin-4-yl]-benzylaminetrifluoroacetate

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-naphthalen-2-yl-methanonetrifluoroacetate)

By proceeding in a similar manner to the method described in EXAMPLE 20,but using 2-naphthoic acid in place of indole-6-carboxylic acid, therewas prepared the title compound as a yellow oil. LC-MS: R_(T)=3.66minutes (100% by ELSD); MS (ES⁺), 345 (MH⁺).

EXAMPLE 233-{1-[3-(2-naphthylthio)propionyl]-piperidin-4-yl}-benzylaminetrifluoroacetate

(A.K.A.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-3-(naphthalen-2-ylsulfanyl)-propan-1-onetrifluoroacetate)

By proceeding in a similar manner to the method described in EXAMPLE 20,but using 3-(2-naphthylthio)propionic acid in place ofindole-6-carboxylic acid, there was prepared the title compound as ayellow oil. LC-MS: R_(T)=4.00 minutes (>95% by ELSD); MS (ES⁺),405(MH⁺).

EXAMPLE 24 3-{1-[4-(indol-3-yl)butanoyl]-piperidin-4-yl}-benzylaminetrifluoroacetate

(A.K.A.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-4-(1H-indol-3-yl)-butan-1-onetrifluoroacetate)

By proceeding in a similar manner to the method described in EXAMPLE 20,but using 4-(indol-3-yl)butanoic acid in place of indole-6-carboxylicacid, there was prepared the title compound as a yellow oil. LC-MS:R_(T)=3.64 minutes (>90% by ELSD); MS (ES⁺), 376(MH⁺).

EXAMPLE 253-{1-[4-(4-biphenyl)-4-ketobutanoyl]-piperidin-4-yl}-benzylaminetrifluoroacetate

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-biphenyl-4-yl-methanonetrifluoroacetate)

By proceeding in a similar manner to the method described in EXAMPLE 20,but using 4-(4-biphenyl)-4-ketobutanoic acid in place ofindole-6-carboxylic acid, there was prepared the title compound as ayellow oil. LC-MS: R_(T)=4.00 minutes (100% by ELSD); MS (ES⁺),427(MH⁺).

EXAMPLE 26 3-[1-(3-benzyloxybenzoyl)-piperidin-4-yl]-benzylaminetrifluoroacetate

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(3-benzyloxy-phenyl)-methanonetrifluoroacetate)

By proceeding in a similar manner to the method described in EXAMPLE 23,but using 3-benzyloxybenzoic acid in place of indole-6-carboxylic acid,there was prepared the title compound as a yellow oil. LC-MS: R_(T)=3.87minutes (100% by ELSD); MS (ES⁺), 401 (MH⁺).

EXAMPLE 273-[1-(5-phenylethynyl-thiophene-2-carbonyl)-piperidin-4-yl]-benzylaminetrifluoroacetate

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(5-phenylethynyl-thiophen-2-yl)-methanonetrifluoroacetate)

By proceeding in a similar manner to the method described in EXAMPLE 20,but using 5-phenylethynyl-thiophene-2-carboxylic acid in place ofindole-6-carboxylic acid, there was prepared the title compound as ayellow oil. LC-MS: R_(T)=4.09 minutes (>97% by ELSD); MS(ES⁺), 410(MH⁺).

EXAMPLE 283-[1-(4-phenylethynyl-thiophene-2-carbonyl)-piperidin-4-yl]-benzylaminetrifluoroacetate

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(4-phenylethynyl-thiophen-2-yl)-methanonetrifluoroacetate)

By proceeding in a similar manner to the method described in EXAMPLE 20,but using 4-phenylethynyl-thiophene-2-carboxylic acid in place ofindole-6-carboxylic acid, there was prepared the title compound as ayellow oil. LC-MS: R_(T)=4.08 minutes (>96% by ELSD); MS(ES⁺), 401(MH⁺).

EXAMPLE 29 3-(1-Benzoyl-piperidin-4-yl)-benzylamine trifluoroacetate

(A.K.A. [4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-phenyl-methanonetrifluoroacetate)

By proceeding in a similar manner to the method described in EXAMPLE 20,but using benzoic acid in place of indole-6-carboxylic acid, there wasprepared the title compound as a yellow oil. LC-MS: R_(T)=3.39 minutes(>95% by ELSD); MS(ES⁺) 295(MH⁺).

EXAMPLE 30 3-[1-(4-N,N-dimethylaminobenzoyl)-piperidin-4-yl]-benzylaminetrifluoroacetate

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(4-dimethylamino-phenyl)-methanonetrifluoroacetate)

By proceeding in a similar manner to the method described in EXAMPLE 20,but using 4-N,N-dimethylaminobenzoic acid in place ofindole-6-carboxylic acid, there was prepared the title compound as ayellow oil. LC-MS: R_(T)=3.32 minutes (100% by ELSD); MS(ES⁺) 338(MH⁺).

EXAMPLE 316-fluoro-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylaminedi-hydrochloride

(A.K.A.[4-(3-Aminomethyl-4-fluoro-phenyl)-piperidin-1-yl]-(5-phenethyl-pyridin-3-yl)-methanonedi-hydrochloride)

By proceeding in a similar manner to the method described in EXAMPLE 17,but using 3-bromo-6-fluoro-benzylamine in place of3-bromo-4-fluoro-benzylamine, there was prepared the title compound as apale yellow oil. ¹H NMR [(CD₃)₂SO, 500 MHz]: δ8.44 (m, 2H), 7.61 (s,1H), 7.40 (m, 1H), 7.20 (m, 6H), 7.05 (m, 1H), 4.62 (br m, 1H), 3.98 (m,2H), 3.45 (br m, 1H), 3.20 (br m, 1H), 3.07 (m, 2H), 3.00 (m, 2H), 2.95(m, 2H) 1.80 (br m, 1H), 1.70 (br m, 3H). MS(EI): 418(M⁺+H).

EXAMPLE 321-{3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-phenyl)ethylaminedi-hydrochloride

(A.K.A.{4-[3-(1-Amino-ethyl)-phenyl]-piperidin-1-yl}-(5-phenethyl-pyridin-3-yl)-methanonedi-hydrochloride)

By proceeding in a similar manner to the method described in EXAMPLE 17,but using 1-(3-bromophenyl)ethylamine (prepared according to theprocedure of C. P. Chen et al., Tetrahedron Letters, 199, 32(49), pages7175-7178) in place of 3-bromo-4-fluoro-benzylamine, there was preparedthe title compound as a white solid. ¹H NMR[(CD₃)₂SO, 500 MHz]: δ8.62(m, 2H), 7.95 (s, 1H), 7.50 (s, 1H), 7.20 (m, 8H), 4.62 (br m, 1H), 4.38(t, J=6 Hz, 1H), 3.50 (m, 1H), 3.45 (br m, 1H), 3.20 (br m, 1H), 3.07(m, 2H), 3.00 (m, 2H), 2.95 (m,2H), 1.87 (br m, 1H), 1.65 (br m, 3H),1.50 (d, J=6 Hz, 3H). MS(EI): 414(M⁺+H).

EXAMPLE 333-[1-(4-hydroxy-quinoline-3-carbonyl)-piperidin-4-yl]-benzylamine

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(4-hydroxy-quinolin-3-yl)-methanone)

By proceeding in a similar manner to the method described in EXAMPLE 1,but using 4-hydroxy-quinoline-3-carboxylic acid (prepared according tothe procedure of K. J. Shah, and E. A. Coats, J. Med. Chem., 1977,20(8), pages 1001-1006) in place of5-phenylethynyl-pyridine-3-carboxylic acid, there was prepared the titlecompound as a white amorphous solid. ¹H NMR[(CD₃)₂SO, 500 MHz]: δ8.10(m, 2H), 7.68 (m, 1H), 7.59 (m, 1H), 7.36 (m, 3H), 7.22 (m, 2H), 4.65(br m, 1H), 4.00 (m, 2H), 3.80 (br m, 1H), 3.35 (br m, 1H), 3.10 (br m,1H), 3.00 (br m, 1H), 1.90-1.75 (br m, 4H). MS(EI): 362(M⁺+H).

EXAMPLE 343-[1-(6-phenyl-quinoline-3-carbonyl)-piperidin-4-yl]-benzylaminedi-hydrochloride

(A.K.A.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(6-phenyl-quinolin-3-yl)-methanonedi-hydrochloride)

By proceeding in a similar manner to the method described in EXAMPLE 1,but using 6-phenyl-quinoline-3-carboxylic acid [prepared according tothe procedure of J.Biwersi et al., Am. J. Physiol., 1992, 262(1, Pt. 1),C243-C250] in place of 5-phenylethynyl-pyridine-3-carboxylic acid, therewas prepared the title compound as a white amorphous solid. ¹HNMR[(CD₃)₂SO, 500 MHz]: δ9.00 (s, 1H), 8.59 (s, 1H), 8.41 (s, 1H), 8.10(m, 2H), 7.85 (m, 2H), 7.58 (m, 2H), 7.45 (m, 2H), 7.34 (m, 3H), 4.75(br m, 1H), 4.00 (m, 2H), 3.80 (br m, 1H), 3.35 (br m, 1H), 3.00 (br m,1H), 2.90 (br m, 1H), 1.90-1.75 (br m, 4H). MS(EI): 422(M⁺+H).

EXAMPLE 354-(3-aminomethyl-phenyl)-1-(5-phenethyl-pyridine-3-carbonyl)-piperidine-4-carbonitrile

A. 3-Cyanobenzylcyanide

To a solution of 9.8 g (200 mmole) of sodium cyanide and 1.61 g (5mmole) of tetrabutylammonium bromide in 50 ml of water was added asolution of 19.61 g (100 mmole) of α-bromo-m-tolunitrile in 150 ml ofdichloromethane. The mixture was stirred at room temperature for 24hours. To this mixture was added 6.2 ml (100 mmole) of iodomethane. Themixture was stirred at room temperature for 3 hours. The layers wereseparated and the organic layer was dried over magnesium sulfate and wasfiltered. The filtrate was evaporated and the residue was trituratedwith petroleum ether and the insoluble material was collected to give14.5 g of a white solid, mp-66-9° C.; 100% yield: ¹H-NMR (300 MHz,CDCl₃) δ (TMS) 3.80-3.90(s, 2H), 7.49-7.72(m, 4H).

B. N-tert-Butoxycarbonyl-bis(2-chloroethyl)amine

To a mixture of 17.85 g (100 mmole) of bis(2-chloroethyl)aminehydrochloride and 24.0 g (110 mmole) of di-tert-butyl dicarbonate in 100ml of dichloromethane was added a solution of 15.3 ml (110 mmole) oftrietylamine in 50 ml of dichloromethane dropwise over 30 minutes. Themixture was stirred at room temperature for 24 hours and was poured intowater. The organic layer was dried over magnesium sulfate and wasfiltered. The filtrate was evaporated to give 24 g of an oil, 100%yield: ¹H-NMR (300 MHz, CDCL₃) δ (TMS) 1.37-1.56 (m, 9H), 3.50-3.62 (m,8H); MS (ESI) m/e 242 (M+H)⁺.

C. 4-(3-Cyanophenyl)-1-tert-butoxycarbonyl-piperidine-4-carbonitrile

To a solution of 2.8 g (19.7 mmole) of 3-cyanobenzylnitrile and 4.77 g(19.7 mmole) of N-tert-butylcarbonyl-bis(2-chloroethyl)amine in 100 mlof anhydrous DMF was added 2.36 g (59.1 mmole) of 60% sodium hydride inportions over 10 minutes. The mixture was stirred at room temperaturefor 3 days and was poured into water and was extracted with ether. Theether layer was dried over magnesium sulfate and was filtered. Thefiltrate was evaporated and the residue was purified by flashchromatography using 4:1 hexane:ethyl acetate to give the product as awhite solid: ¹H-NMR (300 MHz, CDCl₃) δ (TMS) 1.45(s, 9H), 1.85-2.0(m,2H), 2.0-2.28(m, 2H), 3.05-3.30(m, 2H), 4.12-4.4(m, 2H), 7.53-7.80(m,4H).

D.4-(3-Aminomethyl-phenyl)-1-tert-butoxycarbonyl-piperidine-4-carbonitrile

To a mixture of 0.31 g (1 mmole) of4-(3-cyanophenyl)-1-tert-butoxycarbonyl-piperidine-4-carbonitrile in 30ml of absolute ethanol was added 0.08 ml (1 mmole) of conc. hydrochloricacid followed by 30 mg of 5% Pd/C. The mixture was agitated in a Parrshaker for 3 hours at 30 lbs. of pressure of hydrogen. The mixture wasfiltered through celite and the filtrate was evaporated. The residue wastreated with ether and was stirred for 30 minutes and was filtered. Thefilter cake was treated with aqueous sodium carbonate and was extractedwith dichloromethane to give 0.2 g of product: ¹H-NMR (300 MHz, CDCl₃) δ(TMS) 1.38-1.60(m, 9H), 1.88-2.18(m, 4H), 3.05-3.30(m, 4H), 3.79-4.0(m,2H), 7.22-7.85(m, 4H); MS (ESI) m/e 316 (M+H)⁺.

E.4-(3-Benzyloxycarbonylaminomethyl-phenyl)-1-tert-butoxycarbonyl-piperidine-4-carbonitrile

To a solution of 0.2 g of4-(3-Aminomethyl-phenyl)-1-tert-butoxycarbonyl-piperidine-4-carbonitrilein 15 ml of dichloromethane was added a few drops of triethylaminefollowed by a few drops of benzyl chloroformate. The mixture was stirredfor 1 hour at room temperature and was poured into aqueous sodiumcarbonate and was extracted with dichloromethane. The organic layer wasdried over magnesium sulfate and was filtered. The filtrate wasevaporated and the residue was used directly in the next step withoutfurther purification: ¹H-NMR (300 MHz, CDCL₃) δ (TMS) 1.39-1.52 (m, 9H),1.80-2.16(m, 4H), 3.08-3.42(m, 4H), 4.19-4.50(m, 2H), 5.08-5.13(d, 2H),7.28-7.79(m, 9H); MS (ESI) m/e 450 (M+H)⁺.

F. 4-(3-Benzyloxycarbonylaminomethyl-phenyl)-piperidine-4-carbonitrile

The residue from the previous step was dissolved in dichloromethanecontaining 1 ml of trifluoroacetic acid and the solution was stirred atroom temperature for 45 minutes. The solution was poured into aqueoussodium carbonate and was extracted with dichloromethane. The organiclayer was dried and evaporated and the residue was purified by flashchromatography using 7:3 hexane:ethyl acetate to give the product:¹H-NMR (300 MHz, CDCL₃) δ (TMS) 1.80-2.18(m, 4H), 3.07-3.35(m, 4H),4.28-4.50(m, 2H), 5.09-5.13(d, 2H), 7.10-7.77(m, 9H); MS (ESI) m/e 349(M+H)⁺.

G.4-(3-Benzyloxycarbonylaminomethyl-phenyl)-1-(5-phenethyl-pyridine-3-carbonyl)-piperidine-4-carbonitrile

To a solution of 0.15 g (0.33 mmole) of4-(3-benzyloxycarbonylaminomethyl-phenyl)-piperidine-4-carbonitrile in20 ml of acetonitrile was added 0.038 g (0.33 mmole) of N-ethylmopholinefollowed by 0.11 g (0.33 mmole) of TBTU. To this solution was added0.075 g (0.33 mmole) of 5-phenethylpyridine-3-carboxylic acid inportions over 10 minutes. The mixture was stirred for 2 hours. Thesolution was concentrated and the residue was purified by flashchromatography using 95:5 dichloromethane:methanol to provide 0.2 g ofproduct: ¹H-NMR (300 MHz, CDCL₃) δ (TMS) 1.79-2.20 (m, 4H), 2.70-2.82(m, 4H), 2.90-3.07 (m, 2H), 3.15-3.70 (m, 2H), 4.35-4.40 (d, 2H),5.07-5.25 (d, 2H), 7.10-7.50 (m, 15H), 8.42-8.58 (m, 2H); MS (ESI) m/e559 (M+H)⁺.

H.4-(3-Aminomethyl-phenyl)-1-(5-phenethyl-pyridine-3-carbonyl)-piperidine-4-carbonitrileTo a solution of 0.15 g of4-(3-benzyloxycarbonylaminomethyl-phenyl)-1-(5-phenethyl-pyridine-3-carbonyl)-piperidine-4-carbonitrilein 5 ml of glacial acetic acid was added 1 ml of 30% HBr in acetic acid.The solution was stirred at room temperature for 2 hours. The solutionwas poured into a saturated sodium carbonate solution and was extractedwith dichloromethane. The organic layer was dried over magnesium sulfateand was filtered and evaporated. The residue was purified by Rainin HPLCusing 10-100% (acetonitrile—0.1% aqueous TFA) to yield 16 mg of productisolated as the trifluoroacetic acid salt:¹H-NMR (300 MHz, DMSO-d₆) δ(TMS); 1.95-2.30 (m, 4H), 2.45-2.62(m, 2H), 2.88-3.12(m, 4H), 3.70-4.20(m, 2H), 7.12-7.38(m, 4H), 7.45-7.82(m, 6H), 8.50-8.65(m, 2H); MS (ESI)m/e 425 (M+H)⁺.

EXAMPLE 36[4-(3-aminomethylphenyl)piperidin-1-yl]-(3,4-dichlorophenyl)methanonetrifluoroacetate

TFP resin (125 mg of 1.25 mmol/g resin, with 100% loading of acid, 156mmol, prepared according to the procedure described by J. M. Salvino et.al. in International Patent Application Publication No. WO 99/67228) wasswollen in dichloromethane (2.5 mL) for 15 minutes then treated with asolution of 4-(3-aminomethylphenyl)piperidine (40 mg, 100 mmol) indichloromethane (2.5 mL). The mixture was sealed in the reaction vesselthen left shaking for 8 hours. The resin was filtered, then washed withdichloromethane (2 mL) [TLC (5% MeOH/EtOAc) showed single product spot(no baseline amine)] and then treated with trifluoroacetic acid (0.5mL). After shaking for 2 hours TLC showed no residual intermediate andthe reaction mixture was evaporated. The residue [97% purity by HPLC:R_(T)=7.32 minutes; 10 micron C₁₈ reverse phase column (4.6 mm×10cm)eluting with 10-100% acetonitrile and water containing 0.1%trifluoroacetic acid] was dissolved in water (50 mL) and the solutionwas lyophilized to give the title compound as an amorphous solid. ¹H NMR[(CD₃)₂SO]: δ8.15 (br s, 3H), 7.72-7.69 (m, 2H), 7.40 (dd, 1H),7.36-7.25 (m, 4H), 4.66-4.51 (m, 1H), 4.05-3.96 (m, 2H), 3.69-3.48 (m,1H), 3.30-3.11 (m, 1H), 2.91-2.73 (m, 2H), 1.90-1.54 (m, 4H). MS(Ionspray): 363 and 365(M⁺+1).

EXAMPLE 371-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(2-phenoxy-phenyl)-methanonetrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 36,but using the 2-phenoxybenzoic acid derived TFP resin in place of the3,4-dichlorobenzoic acid TFP resin, there was prepared the titlecompound as a white amorphous solid. ¹H NMR [(CD₃)₂SO]: δ8.11 (br s, 3H,NH₃ ⁺); 7.43-7.04 (m, 1OH); 7.02-6.85 (m, 3H); 4.65-4.52 (m, H);4.05-3.90 (m, 2H); 3.62-3.49 (m, H); 3.21-3.05 (m, H); 2.86-2.66 (m,2H); 1.87-1.30 (m, 4H). MS(Ion spray): 587 (M⁺+1).

EXAMPLE 381-{1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-3-methylsulfanyl-6,7-dihydro-5H-benzo[c]thiophen-4-onetrifluoroacetate

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate(TBTU) (120 mg, 0.38 mmol) was added to a room temperature solution of3-methylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid (88 mg, 0.36 mmol) and diisopropylethylamine (140 mg, 1.08 mmol) indimethylformamide (2 mL), under nitrogen. The reaction mixture wasstirred for 10 minutes at room temperature before adding a solution of4-[3-(N,N-di-tert-butoxycarbonylaminomethyl)phenyl]piperidine (140 mg,0.36 mmol) and diisopropylethylamine (140 mg, 1.08 mmol) indimethylformamide (2 mL). The reaction mixture was stirred at roomtemperature for 16 hours, concentrated to dryness in vacuo, andsubjected to dry flash column chromatography on silica with 50:50,dichloromethane:ethyl acetate.1-{1-[4-(3-(N,N-di-tert-butoxycarbonylaminomethyl)phenyl)-piperidin-1-yl]-methanoyl}-3-methylsulfanyl-6,7-dihydro-5H-benzo[c]thiophen-4-onewas isolated as a colorless oil (177 mg). The intermediate was dissolvedin dichloromethane (20 mL), cooled at 0° C., and treated withtrifluoroacetic acid (2 mL). The reaction mixture was stirred at roomtemperature under nitrogen for 2 hours, and concentrated to dryness invacuo. The residue was dissolved in 20% acetonitrile/water [containing0.1% trifluoroacetic acid] (9 mL) and purified by preparativereverse-phase HPLC (C-18, 10 micron reverse-phase column), eluting with10% to 100% acetonitrile/water (containing 0.1% trifluoroacetic acid).The product fractions were combined and the acetonitrile removed invacuo. The aqueous residue was frozen and lyophilized to give the titlecompound as an amorphous white solid (122 mg, 64%). ¹H NMR [(CD₃)₂SO]:δ8.16 (br s, 3H, NH₃ ⁺); 7.41-7.24 (m, 4H); 4.21 (br d, 2H); 4.03 (q,2H); 3.18-3.02 (m, 2H); 2.91-2.72 (m, 3H); 2.59 (s, 3H); 2.53-2.41 (m,2H); 1.98-1.90 (m, 2H); 1.90-1.79 (m, 2H); 1.68-1.50 (m, 2H). MS(Ionspray): 415 (M⁺+1).

EXAMPLE 391-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(6-chloro-benzo[b]thiophen-2-yl)-methanonetrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 6-chlorobenzo[b]thiophene-2-carboxylic acid (preparedaccording to the procedure described in International Patent ApplicationNo. WO 0107436) in place of3-methylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid, there was prepared the title compound as an amorphous white solid.¹H NMR [(CD₃)₂SO]: δ8.17 (d, H); 8.14 (br s, 3H, NH₃ ⁺); 7.91 (d, H);7.73 (s, H); 7.45 (dd, H); 7.37 (s, H); 7.35-7.24 (m, 3H); 4.42 (br s,2H); 4.00 (q, 2H); 3.12 (br s, 2H); 2.93-2.79 (m, H); 1.89-1.77 (m, 2H);1.70-1.55 (m, 2H). MS(Ion spray): 385 and 387 (M⁺+1).

EXAMPLE 401-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(5-chloro-1H-indol-2-yl)-methanonetrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 5-chloro-1H-indole-2-carboxylic acid in place of3-methylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid, there was prepared the title compound as an amorphous white solid.¹H NMR [(CD₃)₂SO]: δ11.78 (s, H); 8.14 (br s, 3H, NH₃ ⁺); 7.63 (s, H);7.43-7.22 (m, 5H); 7.16 (dd, H); 6.76 (s, H); 4.55 (br d, 2H); 4.00 (q,2H); 3.14 (br s, 2H); 2.94-2.80 (m, H); 1.90-1.79 (m, 2H); 1.73-1.54 (m,2H); MS(Ion spray): 368 and 370 (M⁺+1).

EXAMPLE 411-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(8-chloro-4H-1,5-dithia-cyclopenta[a]naphthalen-2-yl)-methanonetrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 8-chloro-4H-1,5-dithiacyclopenta[a]naphthalene-2-carboxylicacid in place of3-methylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid, there was prepared the title compound as an amorphous white solid.¹H NMR [(CD₃)₂SO]: δ8.14 (br s, 3H, NH₃ ⁺); 7.52 (d, H); 7.44-7.23 (m,7H); 4.45 (s, 2H); 4.43 (br d, 2H); 4.00 (q, 2H); 3.12 (br s, 2H);2.95-2.80 (m, H); 1.90-1.78 (m, 2H); 1.72-1.56 (m, 2H). MS(Ion spray):453 and 455 (M⁺+1).

EXAMPLE 421-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(2′,4′-difluoro-4-hydroxy-biphenyl-3-yl)-methanonetrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using diflunisal in place of3-methylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid, there was prepared the title compound as an amorphous white solid.¹H NMR [(CD₃)₂SO]: δ10.15 (s, H, OH); 8.15 (br s, 3H, NH₃ ⁺); 7.56-7.46(m, H); 7.40-7.22 (m, 7H); 7.13 (td, H); 6.97 (d, H); 4.64 (br s, H);3.98 (q, 2H); 3.51 (br s, H); 3.10 (br s, H); 2.88-2.71 (m, H);1.90-1.46 (m, 4H). MS(Ion spray): 423 and 424 (M⁺+1).

EXAMPLE 431-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(3-methylsulfanyl-6,7-dihydro-benzo[c]thiophen-1-yl)-methanonetrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 3-methylsulfanyl-6,7-dihydro-benzo[c]thiophene-1-carboxylicacid in place of3-methylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid, there was prepared the title compound as an amorphous white solid.¹H NMR [CDCl₃9 : δ8.13 (br s, 3H, NH₃ ⁺); 7.38-7.30 (m, H); 7.27-7.18(m, 3H); 6.68 (d, H); 6.11-6.04 (m, H); 4.52-4.25 (br m, 2H); 4.01-3.93(br m, 2H); 3.40-3.38 (m, H); 3.12-2.97 (m, H); 2.90-2.75 (m, H); 2.75(t, 2H); 2.43 (s, 3H); 2.37-2.28 (m, 2H); 1.97-1.81 (m, 2H); 1.89-1.60(m, 2H). MS(Ion spray): 400 (M⁺+1).

EXAMPLE 44 1-{1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-6,6-dimethyl-3-methylsulfanyl-6,7-dihydro-5H-benzo[c]thiophen-4-onetrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using6,6-dimethyl-3-methylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid in place of3-methylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid, there was prepared the title compound as an amorphous white solid.¹H NMR [(CD₃)₂SO]: δ8.16 (br s, 3H, NH₃ ⁺); 7.40-7.34 (m, 2H); 7.32-7.26(m, 2H); 4.20 (br d, 2H); 4.01 (br s, 2H); 3.20-3.06 (m, 2H); 2.93-2.80(m, H); 2.67 (s, 2H); 2.60 (s, 3H); 2.38 (3, 2H); 1.89-1.78 (m, 2H);1.67-1.50 (m, 2H); 0.98 (s, 6H). MS(Ion spray): 444 (M⁺+1).

EXAMPLE 451-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(6-bromo-pyridin-3-yl)-methanonebistrifluoroacetate

A. 6-Bromonicotinic acid hydrochloride

n-Butyllithium (8.0 mL of 2.5M in hexanes, 20 mmol) was added dropwiseto a stirring solution of 2,5-dibromopyridine (4.74 g, 20 mmol) in THF(100 mL) at −100° C., under nitrogen. The reaction mixture was left atthis temperature for 30 minutes before bubbling anhydrous carbon dioxidegas through the reaction mixture (for 20 minutes), and leaving to warmto −20° C. Quenched with 1N HCl (20 mL) and brine (20 mL), and extractedinto ethyl acetate, dried over magnesium sulfate, concentrated todryness. 6-Bromonicotinic acid hydrochloride was isolated as a paleyellow powder (3.8 g, 16 mmol). ¹H NMR [CDCl₃+CD₃OD]: δ8.86 (d, 1H),8.07 (dd, 1H), 7.52 (d, 1H). MS(Ion spray): 202 and 204 (M⁺+1).

B.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(6-bromo-pyridin-3-yl)-methanonebistrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 6-bromonicotinic acid hydrochloride in place of3-methylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid, there was prepared the title compound as an amorphous white solid.¹H NMR [CD₃OD]: δ8.48 (d, H); 7.89 (dd, H); 7.82 (d, H); 7.48-7.30 (m,4H); 4.90-4.81 (m, H); 4.15 (s, 2H); 3.84 (br d, H); 3.46-3.36 (m, H);3.11-2.91 (m, 2H); 2.13-1.68 (m, 4H). MS(Ion spray): 374 and 376 (M⁺+1).

EXAMPLE 466-{1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-2,3-dihydro-thiazolo[3,2-a]pyrimidin-5-one

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylicacid in place of3-methylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid, there was prepared the title compound as an amorphous white solid.¹H NMR [CD₃OD]: δ7.97 (s, H); 7.44-7.29 (m, 4H); 4.76 (br d, H);4.59-4.51 (m, 2H); 4.07 (s, 2H); 3.83 (br d, H); 3.69-3.57 (m, 2H);3.41-3.21 (m, H); 3.02-2.85 (m, 2H); 2.05-1.67 (m, 4H). MS(Ion spray):371 (M⁺+1).

EXAMPLE 471-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(3-chloro-phenyl)-methanonetrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 3-chlorobenzoic acid in place of3-methylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid, there was prepared the title compound as an amorphous white solid.¹H NMR [(CD₃)₂SO]: δ8.14 (br s, 3H, NH₃ ⁺); 7.57-7.43 (m, 3H); 7.40-7.22(m, 5H); 4.70-4.56 (m, H); 4.01 (q, 2H); 3.64-3.56 (m, H); 3.23-3.10 (m,H); 2.91-2.79 (m, 2H); 1.92-1.52 (m, 4H). MS(Ion spray): 329 and 331(M⁺+1).

EXAMPLE 481-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(4-chloro-phenyl)-methanonetrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 4-chlorobenzoic acid in place of3-methylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid, there was prepared the title compound as an amorphous white solid.¹H NMR [(CD₃)₂SO]: δ8.15 (br s, 3H, NH₃ ⁺); 7.53 (d, 2H); 7.44 (d, 2H);7.40-7.23 (m, 4H); 4.64-4.56 (m, H); 4.02 (q, 2H); 3.72-3.58 (m, H);3.24-3.10 (m, H); 2.95-2.89 (m, 2H); 1.90-1.50 (m, 4H). MS(Ion spray):329 and 331 (M⁺+1).

EXAMPLE 491-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-phenyl}-methanonetrifluoroacetate

A. 3-[5-(2-Chlorophenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid methylester

3-(2H-Tetrazol-5-yl)-benzoic acid methyl ester (204 mg, 1 mmol)(prepared by the method of Tanaka et al, J. Med. Chem., 1998, 41(13),2406) and 2-chlorobenzoyl chloride (175 mg, 1 mmol) were combined inanisole (10 mL) at room temperature and 2,4,6-collidine (121 mg, 1 mmol)in anisole (1 mL) was added. The reaction mixture was heated at 100° C.for 1 hour followed by 120° C. for 15 minutes, monitoring the evolutionof gas by balloon [volume of gas evolved was measured by positivedisplacement of water, total=22 mL]. Cooled reaction mixture to roomtemperature, and concentrated to dryness in vacuo. The residue wassubjected to flash column chromatography on silica with gradientdilution 5% to 40% ethyl acetate/heptane.3-[5-(2-Chlorophenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid methyl esterwas isolated as a colorless powder (229 mg, 73%). ¹H NMR [CDCl₃]: 8.79(s, H); 8.36 (d, H); 8.25 (d, H); 8.14 (d, H); 7.72-7.57 (m, 2H);7.57-7.41 (m, 2H); 4.00 (s, 3H). MS(Ion spray): 315 and 317 (M⁺+1).

B.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-phenyl}-methanonetrifluoroacetate

1N Sodium hydroxide (2 mL, 2 mmol) was added to a solution of3-[5-(2-chlorophenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid methyl ester(113 mg, 0.36 mmol) in methanol (5 mL) and THF (2 mL), and the reactionmixture stirred at room temperature for 2 h, before neutralizing to pH 7with 1N hydrochloric acid. The solution was concentrated to dryness invacuo and placed under high vacuum overnight. Crude material was useddirectly without purification [MS(Ion spray): 301 and 303 (M⁺+1); LC/ MSpurity >95%, only major impurity is sodium chloride].2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate(TBTU) (116 mg, 0.36 mmol) was added to a room temperaturesolution/suspension of crude3-[5-(2-chlorophenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid anddiisopropylethylamine (150 mg, 1.14 mmol) in dimethylformamide (2 mL),under nitrogen. The reaction mixture was stirred for 10 minutes at roomtemperature before adding a solution of4-[3-(N,N-di-tert-butoxycarbonylaminomethyl)phenyl]piperidine (78 mg,0.2 mmol) and diisopropylethylamine (150 mg, 1.14 mmol) indimethylformamide (2 mL). The reaction mixture was stirred at roomtemperature for 16 hours, concentrated to dryness in vacuo, andsubjected to dry flash column chromatography on silica with 50:50,dichloromethane:ethyl acetate.1-{4-[3-(N,N-di-tert-butoxycarbonylaminomethyl)phenyl]-piperidin-1-yl}-1-{3-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-phenyl}-methanonewas isolated as a colorless oil, which was dissolved in dichloromethane(10 mL), cooled at 0° C., and treated with trifluoroacetic acid (l mL).The reaction mixture was stirred at room temperature under nitrogen for2 hours, and concentrated to dryness in vacuo. The residue was dissolvedin 20% acetonitrile/water [containing 0.1% trifluoroacetic acid] (9 mL)and purified by preparative reverse-phase HPLC (C-18, 10 micronreverse-phase column), eluting with 20% to 60% acetonitrile/water(containing 0.1% trifluoroacetic acid). The product fractions werecombined and concentrated to dryness in vacuo. The title compound wasisolated as an amorphous white glass solid (98 mg, 83%). ¹H NMR[(CD₃)₂SO]: δ8.16 (br s, 3H, NH₃ ⁺) overlapped with 8.22-8.16 (m, 2H)and 8.13 (s, H); 7.79-7.72 (m, 3H); 7.69 (td, H); 7.62 (td, H); 7.41 (s,H); 7.39-7.27 (m, 3H); 4.64 (br d, H); 4.03 (q, 2H); 3.79-3.63 (m, H);3.28-3.20 (m, H); 3.03-2.80 (m, 2H); 1.96-1.57 (m, 4H). MS(Ion spray):473 and 475 (M⁺+1).

EXAMPLE 501-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(5-pyridin-3-yl-[1,3,4]oxadiazol-2-yl)-phenyl]-methanonebistrifluoroacetate

A. 3-(5-Pyridin-3-yl-[1,3,4]oxadiazol-2-yl)-benzoic acid methyl ester

Prepared in a similar manner to the method described in EXAMPLE 49A, butusing nicotinoyl chloride hydrochloride instead of 2-chlorobenzoylchloride, 2 mmol of 2,4,6-collidine, and heating at 110° C. instead of100° C. The residue was subjected to flash column chromatography onsilica with ethyl acetate and 5% methanol/ethyl acetate.3-(5-Pyridin-3-yl-[1,3,4]oxadiazol-2-yl)-benzoic acid methyl ester wasisolated as a colorless powder (84 mg, 30%). ¹H NMR [CDCl₃]: 9.40 (s,H); 8.84-8.80 (m, H); 8.80-8.78 (m, H); 8.47 (dt, H); 8.38 (dt, H); 8.26(dt, H); 7.67 (t, H); 7.52 (dd, H); 4.00 (s, 3H). MS(Ion spray): 282(M⁺+1).

B.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(5-pyridin-3-yl-[1,3,4]oxadiazol-2-yl)-phenyl]-methanonebistrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE49B, but using 3-(5-pyridin-3-yl-[1,3,4]oxadiazol-2-yl)-benzoic acidmethyl ester in place of3-[5-(2-chlorophenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid methyl ester,there was prepared the title compound as an amorphous white glass solid.¹H NMR [(CD₃)₂SO]: δ9.37 (br s, H); 8.86 (br s, H); 8.55 (d, H);8.28-8.23 (m, H); 8.20 (s, H); 8.16 (br s, 3H, NH₃ ⁺); 7.79-7.65 (m,3H); 7.41 (s, H); 7.39-7.26 (m, 3H); 4.63 (br d, H); 4.09-4.00 (m, 2H);3.80-3.62 (m, H); 3.37-3.16 (m, H); 3.02-2.80 (m, 2H); 1.98-1.55 (m,4H). MS(Ion spray): 441 (M⁺+1).

EXAMPLE 511-{1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-3-ethylsulfanyl-6,6-dimethyl-6,7-dihydro-5H-benzo[c]thiophen-4-onetrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE49B, but using3-ethylsulfanyl-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid methyl ester in place of3-[5-(2-chlorophenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid methyl ester,there was prepared the title compound as an amorphous white glass solid.¹H NMR [(CD₃)₂SO]: δ8.16 (br s, 3H, NH₃ ⁺); 7.40-7.33 (m, 2H); 7.32-7.26(m, 2H); 4.30-4.00 (m, 4H); 3.21-3.10 (m, 2H); 3.06 (q, 2H); 2.92-2.80(m, H); 2.66 (s, 2H); 2.38 (s, 2H); 1.90-1.78 (m, 2H); 1.68-1.50 (m,2H); 0.98 (s, 6H). MS(Ion spray): 458 (M⁺+1).

EXAMPLE 521-1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl)-3-propylsulfanyl-6,7-dihydro-5H-benzo[c]thiophen-4-onetrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE49B, but using4-oxo-3-propylsulfanyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid ethyl ester in place of3-[5-(2-chlorophenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid methyl ester,there was prepared the title compound as an amorphous white glass solid.¹H NMR [(CD₃)₂SO]: δ8.14 (br s, 3H, NH₃ ⁺); 7.41-7.23 (m, 4H); 4.21 (brd, 2H); 4.08-3.99 (m, 2H); 3.39-2.99 (m, 4H); 2.94-2.71 (m, 3H);2.54-2.49 (m, 2H); 2.02-1.90 (m, 2H); 1.90-1.70 (m, 4H); 1.70-1.51 (m,2H); 1.03 (t, 3H). MS(Ion spray): 443 (M⁺+1).

EXAMPLE 531-{1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-3-isopropylsulfanyl-6,7-dihydro-5H-benzo[c]thiophen-4-onetrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE49B, but using3-isopropylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid ethyl ester in place of3-[5-(2-chlorophenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid methyl ester,there was prepared the title compound as an amorphous white glass solid.¹H NMR [(CD₃)₂SO]: δ8.14 (br s, 3H, NH₃ ⁺); 7.43-7.23 (m, 4H); 4.30-4.16(m, 2H); 4.09-3.98 (m, 2H); 3.53 (septet, H); 3.22-3.03 (m, 2H);2.93-2.72 (m, 3H); 2.54-2.47 (m, 2H); 2.02-1.86 (m, 4H); 1.70-1.51 (m,2H); 1.42 (d, 6H). MS(Ion spray): 443 (M⁺+1).

EXAMPLE 54 3-{1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-5,5-dimethyl-7-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carbonitriletrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE49B, but using3-cyano-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid ethyl ester in place of3-[5-(2-chlorophenyl)-[1,3,4]oxadiazol-2-yl]-benzoic acid methyl ester,there was prepared the title compound as an amorphous white glass solid.¹H NMR [(CD₃)₂SO]: δ8.14 (br s, 3H, NH₃ ⁺); 7.41-7.33 (m, 2H); 7.32-7.26(m, 2H); 4.30-3.90 (br m, 2H); 4.04-3.98 (m, 2H); 3.30-3.01 (m, 2H);2.93-2.80 (m, H); 2.71 (s, 2H); 2.54 (s, 2H); 1.89-1.76 (m, 2H);1.73-1.51 (m, 2H); 1.01 (s, 6H). MS(Ion spray): 423 (M⁺+1).

EXAMPLE 553-{1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-5,5-dimethyl-7-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid trifluoroacetate

The title compound was isolated as a by-product from the reactioncarried out to synthesize3-{1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-5,5-dimethyl-7-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carbonitriletrifluoroacetate, in EXAMPLE 54. ¹H NMR [(CD₃)₂SO]: δ9.70 (s, H, OH);8.11 (br s, 3H, NH₃ ⁺); 7.42-7.26 (m, 4H); 4.28-3.96 (br m, 2H);4.03-3.99 (m, 2H); 3.27-3.06 (m, 2H); 2.96-2.85 (m, H); 2.70 (s, 2H);2.63 (s, 2H); 1.93-1.72 (m, 2H); 1.69-1.52 (m, 2H); 1.01 (s, 6H). MS(Ionspray): 442 (M⁺+1).

EXAMPLE 563-{1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-5,5-dimethyl-7-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid methyl ester trifluoroacetate

The title compound was isolated as a by-product from the reactioncarried out to synthesize3-{1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-5,5-dimethyl-7-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carbonitriletrifluoroacetate, in EXAMPLE 54. ¹H NMR [(CD₃)₂SO]: δ8.16 (br s, 3H, NH₃⁺); 7.41-7.34 (m, 2H); 7.33-7.27 (m, 2H); 4.30-3.95 (br m, 2H);4.06-4.00 (m, 2H); 3.84 (s, 3H); 3.25-3.04 (m, 2H); 2.94-2.80 (m, H);2.71 (s, 2H); 2.51 (s, 2H); 1.90-1.78 (m, 2H); 1.71-1.51 (m, 2H); 1.00(s, 6H). MS(Ion spray): 456 (M⁺+1).

EXAMPLE 571-{1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-3-methoxy-6,6-dimethyl-6,7-dihydro-5H-benzo[c]thiophen-4-one

By proceeding in a similar manner to the method described in EXAMPLE 38,but using3-Methoxy-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid, there was prepared the title compound as an amorphous white solid.¹H NMR [(CD₃)₂SO]: δ8.22 (br s, 3H, NH₃ ⁺), 7.54-7.27 (m, 4H), 4.29-4.22(m, 2H), 4.14 (s, 3H), 4.13-4.02 (m, 2H), 3.26-3.08 (m, 2H), 3.04-2.86(m, 1H), 2.71 (s, 2H), 2.37 (s, 2H), 2.02-1.84 (m, 2H), 1.79-1.54 (m,2H), 1.04 (s, 6H). MS(Ion spray): 427.3 (M⁺+1).

EXAMPLE 581-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(4-pyrrol-1-yl-phenyl)-methanone-trifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 4-(1H-Pyrrol-1-yl) benzoic acid in place of3-methylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid, there was prepared the title compound as an amorphous white solid.¹H NMR [(CD₃OD]: δ7.62-7.51 (m, 4H), 7.41-7.22 (m, 6H), 6.32-6.28 (m,2H), 4.85-4.66 (m, 2H), 4.08 (s, 2H), 4.03-3.88 (m, 1H), 3.15-2.86 (m,2H), 2.11-1.62 (m, 4H). MS(Ion spray): 360 (M⁺+1).

EXAMPLE 591-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-benzo[b]thiophen-2-yl-methanone-trifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using benzo(b)-thiophene-2-carboxylic acid in place of3-methylsulfanyl-4-oxo-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylicacid, there was prepared the title compound as an amorphous white solid.¹H NMR [(CD₃OD]: δ7.98-7.81 (m, 2H), 7.62 (s, 1H), 7.45-7.32 (m, 5H),7.31-7.22 (m, 1H), 4.80-4.40 (m, 2H), 4.10 (s, 2H), 3.28-3.05 (m, 1H),3.02-2.90 (m, 2H), 2.02-1.88 (m, 2H), 1.86-1.65 (m, 2H). MS(Ion spray):351 (M⁺+1).

EXAMPLE 60(E)-1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-3-(3-methoxy-phenyl)-propenone-trifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 3-methoxycinnamic acid, there was prepared the title compoundas an amorphous white solid. ¹H NMR [(CD₃OD]: δ7.56 (d, 1H), 7.45-7.25(m, 5H), 7.23-7.13 (m, 3H), 6.98-6.90 (m, 1H), 4.85-4.70 (m, 1H),4.50-4.35 (m, 1H), 4.08 (s, 2H), 3.83 (s, 3H), 3.40-3.32 (m, 1H),3.01-2.75 (m, 2H), 2.08-1.83 (m, 2H), 1.81-1.61 (m, 2H). MS(Ion spray):351 (M⁺+1).

EXAMPLE 611-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(3-ethoxy-thiophen-2-yl)-methanone-trifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 3-ethoxythiophene-2-carboxylic acid, there was prepared thetitle compound as an amorphous white solid. ¹H NMR [(CD₃OD]: δ7.53 (d,1H), 7.46-7.22 (m, 4H), 6.94 (d, 1H), 4.60-4.21 (br.m., 2H), 4.19 (q,2H), 4.08 (s, 2H), 3.18-2.98 (m, 1H), 2.96-2.85 (m, 2H), 2.0-1.86 (m,2H), 1.84-1.65 (m, 2H), 1.37 (t, 3H). MS(Ion spray): 345 (M⁺+1).

EXAMPLE 621-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-2-indan-2-yl-ethanone-trifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 2-indanylacetic acid, there was prepared the title compound asan amorphous white solid. ¹H NMR [(CD₃OD]: δ7.45-7.25 (m, 4H), 7.18-7.15(m, 2H), 7.14-7.04 (m, 2H), 4.78-4.65 (m, 1H), 4.18-4.11 (m, 1H), 4.08(s, 2H), 3.28-3.08 (m, 2H), 2.95-2.76 (m, 2H), 2.74-2.58 (m, 6H),2.01-1.85 (m, 2H), 1.75-1.51 (m, 2H). MS(Ion spray): 349 (M⁺+1).

EXAMPLE 631-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[5-(3-chloro-phenyl)-pyridin-3-yl]-methanone-ditrifluoroacetate

A. 5-(3-chlorophenyl)-nicotinic acid

A three neck flask was charged with 5-bromonicotinic acid (2 g, 9.90mmol), 3-chlorophenylboronic acid (1.55 g, 9.90 mmol), a 0.4 M solutionof sodiumcarbonate in water (37 mL, 14.8 mmol) and Acetonitrile (37 mL).The solution was degassed under vacuum and tetrakistriphenylphoshinePd(0) (0.57 g, 0.495 mmol) was added and the reaction refluxed overnightunder nitrogen. The reaction was cooled to room temperature and filteredthrough a celite pad. The filtrate was partially evaporated underreduced pressure and the remaining solution acidified to pH=2 with 1NHCl. The resulting solid was collected by filtration and dried undervacuum. ¹H NMR [(CD₃)₂SO]: δ9.15-9.05 (m, 2H), 8.45 (s, 1H), 7.85 (s,1H), 7.80-7.65 (m, 1H), 7.60-7.42 (m, 2H).

B.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-[5-(3-chloro-phenyl)-pyridin-3-yl]-methanone-ditrifluoroacetate.

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 5-(3-chlorophenyl)-nicotinic acid, there was prepared thetitle compound as an amorphous white solid. ¹H NMR [(CD₃)₂SO]: δ8.99 (s,1H), 8.65 (s, 1H), 8.18 (s, 1H), 8.13 (br.s., 3H, NH₃ ⁺), 7.88 (s, 1H),7.76 (d, 1H), 7.58-7.45 (m, 2H), 7.40-7.20 (m, 4H), 4.80-4.58 (m, 1H),3.98 (q, 2H), 3.78-3.55 (m, 1H), 3.33-3.18 (m, 1H), 2.98-2.71 (m, 2H),1.95-1.52 (m, 4H). MS(Ion spray): 406 (M⁺+1).

EXAMPLE 641-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(5-chloro-benzo[b]thiophen-2-yl)-methanone-trifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 5-chloro-benzo(b)thiophene-2-carboxylic acid, prepared as inWO 0107436, there was prepared the title compound as an amorphous whitesolid. ¹H NMR [(CD₃)₂SO]: δ8.08 (br.s., 3H, NH₃ ⁺), 8.05 (d, 1H), 8.01(s, 1H), 7.68 (s, 1H), 7.47 (d, 1H), 7.40-7.21 (m, 4H), 4.41 (br.s.,2H), 3.99, (q, 2H), 3.30-3.15 (m, 2H), 2.95-2.78 (m, 1H), 1.90-1.75 (m,2H), 1.73-1.52 (m, 2H). MS(Ion spray): 385 (M⁺+1).

EXAMPLE 651-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-2-(3,4-dichloro-phenyl)-ethanone-trifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 3,4-dichlorophenyl acetic acid, there was prepared the titlecompound as an amorphous white solid. ¹H NMR [(CD₃)₂SO]: δ8.08 (br.s.,3H, NH₃ ⁺),7.56 (d, 1H), 7.48 (s, 1H), 7.38-7.15 (m, 5H), 4.58-4.45 (m,1H), 4.15-3.92 (m, 3H), 3.85-3.65 (m, 2H), 3.18-3.03 (m, 1H), 2.85-2.55(m, 2H), 1.80-1.65 (m, 2H), 1.55-1.32 (m, 2H). MS(Ion spray): 376(M⁺+1).

EXAMPLE 661-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-2-(5-chloro-pyridin-3-yloxy)-ethanone-ditrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using (5-chloro-pyridin-3-yloxy)-acetic acid, prepared as in WO0107436, there was prepared the title compound as an amorphous whitesolid. ¹H NMR [(CD₃)₂SO]: δ8.28-8.21 (m, 2H), 8.15 (br.s., 3H, NH₃ ⁺),7.58 (s, 1H), 7.40-7.20 (M, 4H), 5.01 (s, 2H), 4.52-4.38 (m, 1H), 3.98(q, 2H), 3.93-3.80 (m, 1H), 3.22-3.05 (m, 1H), 2.88-2.58 (m, 2H),1.88-1.35 (m, 4H). MS(Ion spray): 360 (M⁺+1).

EXAMPLE 671-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-2-(6-chloro-pyridin-2-yloxy)-ethanone-ditrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using (6-chloro-pyridin-2-yloxy)-acetic acid, prepared as in WO0107436, there was prepared the title compound as an amorphous whitesolid. ¹H NMR [(CD₃)₂SO]: δ8.10 (br.s., 3H, NH₃ ⁺), 7.81-7.71 (m, 1H),7.41-7.18 (m, 4H), 7.08 (d, 1H), 6.88 (d, 1H), 5.15-4.92 (m, 2H),4.50-4.31 (m, 1H), 4.08-3.81 (m, 3H), 3.27-3.08 (m, 1H), 2.92-2.76 (m,1H), 2.75-2.60 (m, 1H), 1.90-1.58 (m, 2H), 1.57-1.35 (m, 2H). MS(Ionspray): 360 (M⁺+1).

EXAMPLE 68(E)-1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-3-(5-chloro-thiophen-2-yl)-propenone-trifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 3-(5-chloro-thiophen-2-yl)-acrylic acid, prepared as in WO0107436, there was prepared the title compound as an amorphous whitesolid. ¹H NMR [(CD₃)₂SO]: δ8.08 (br.s., 3H, NH₃ ⁺), 7.56 (d, 1H),7.40-7.28 (m, 3H), 7.26-7.18 (m, 2H), 7.12 (d, 1H), 6.92 (d, 1H),4.70-4.50 (m, 1H), 4.41-4.21 (m, 1H), 3.98 (q, 2H), 3.28-3.05 (m, 1H),2.90-2.63 (m, 2H), 1.91-1.72 (m, 2H), 1.65-1.35 (m, 2H). ). MS(Ionspray): 361 (M⁺+1).

EXAMPLE 69(E)-1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-3-(4-chloro-thiophen-2-yl)-propenone-trifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 3-(4-chloro-thiophen-2-yl)-acrylic acid, prepared as in WO0107436, there was prepared the title compound as an amorphous whitesolid. 1H NMR [(CD₃)₂SO]: δ8.06 (br.s., 3H, NH₃ ⁺), 7.65 (s, 1H),7.60-7.48 (m, 2H), 7.40-7.20 (m, 4H), 7.08 (d, 1H), 4.70-4.51 (m, 1H),4.42-4.25 (m, 1H), 4.05-3.93 (m, 2H), 3.28-3.08 (m, 1H), 2.90-2.63 (m,2H), 1.90-1.65 (m, 2H), 1.63-1.40 (m, 2H). MS(Ion spray): 361 (M⁺+1).

EXAMPLE 701-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-methanone-trifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 4,5,6,7-tetrahydro-benzo(c)thiophene-1-carboxylic acid,prepared as in JOC V62#6 1997 p. 1599, there was prepared the titlecompound as an amorphous white solid.

¹H NMR [(CD₃)₂SO]: δ8.13 (br.s., 3H, NH₃ ⁺), 7.40-7.33 (m, 2H),7.31-7.25 (m, 2H), 7.20 (s, 1H), 4.35-4.15 (m, 2H), 4.03 (q, 2H),3.17-2.98 (m, 2H), 2.95-2.78 (m, 1H), 2.73-2.58 (m, 4H), 1.90-1.78 (m,2H), 1.75-1.63 (m, 4H), 1.61-1.42 (m, 2H). MS(Ion spray): 355 (M⁺+1).

EXAMPLE 711-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(5-chloro-4-methoxy-thiophen-3-yl)-methanone-trifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 2-chloro-3-methoxy-thiophene-4-carboxylic acid, there wasprepared the title compound as an amorphous white solid. ¹H NMR[(CD₃)₂SO]: δ8.13 (br.s., 3H, NH₃ ⁺), 7.57 (s, 1H), 7.40-7.22 (m, 4H),4.70-4.58 (m, 1H), 4.05 (q, 2H), 3.85 (s, 3H), 3.75-3.60 (m, 1H), 3.25(m, 1H), 2.95-2.78 (m, 2H), 1.93-1.70 (m, 2H), 1.68-1.45 (m, 2H). MS(Ionspray): 365 (M⁺+1).

EXAMPLE 721-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(1H-indol-3-yl)-methanone-trifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using Indole-3-carboxylic acid, there was prepared the titlecompound as an amorphous white solid. ¹H NMR [(CD₃)₂SO]: δ8.13 (br.s.,3H, NH₃ ⁺), 7.78-7.63 (m, 2H), 7.52-7.20 (m, 6H), 7.20-7.03 (m, 2H),4.57-4.38 (m, 2H), 4.03 (q, 2H), 3.17-3.02 (m, 2H), 2.95-2.75 (m, 1H),1.90-1.78 (m, 2H), 1.75-1.57 (m, 2H). MS(Ion spray): 334 (M⁺+1).

EXAMPLE 731-[4-(3-aminomethyl-phenyl)-4-hydroxy-piperidin-1-yl]-1-(5-phenethyl-pyridin-3-yl)-methanone-ditrifluoroacetate

A. 4-(3-Cyano-phenyl)-4-hydroxy-piperidine-1-carboxylic acid-tert-butylester.

A solution of 3-Bromobenzonitrile (0.48 g, 2.64 mmol) in THF (20 mL) wasstirred under nitrogen at −78° C. To this was added dropwise a solutionof 2.0 M nBuLi in hexanes (1.38 mL, 2.72 mmol). The solution was allowedto warm to −15° C. over 1.5 hours. The solution was recooled to −78° C.and a solution of N-Boc-4-piperidone (0.53 g, 2.64 mmol) in THF (5 mL)was added dropwise. The reaction mixture was allowed to warm to −10° C.and stirred at this temperature for three hours. The reaction wasquenched with ½ saturated ammonium chloride solution (30 mL) and stirred15 minutes. The THF was removed by evaporation and the residue extractedwith methylene chloride (3×50 mL). The organic extracts were combined,dried over sodium sulfate, evaporated to give an orange oil which waspurified by flash chromatography 3:5:2 methylene chloride:heptane:ethylacetate to give the title compound (0.30 g) as a clear oil. ¹H NMR[(CDCl₃]: 7.82 (s, 1H), 7.72 (d, 1H), 7.58 (d, 1H), 7.55-7.42 (m, 1H),4.20-3.95 (m, 2H), 3.35-3.10 (m, 2H), 2.08-1.83 (m, 2H), 1.80-1.66 (m,2H), 1.51 (s, 9H).

B.4-[3-(Benzyloxycarbonylamino-methyl)-phenyl]-4-hydroxy-piperidine-1-carboxylicacid-tert-butyl ester.

A solution of 4-(3-Cyano-phenyl)-4-hydroxy-piperidine-1-carboxylicacid-tert-butyl ester (0.30 g, 0.99 mmol) in 7N ammonia/methanol (25 mL)and 5%Rhodium on alumina (0.15 g) was hydrogenated overnight on a Parrapparatus (45 psi). The reaction was filtered through celite,evaporated, and azeotroped with MeOH:toluene 1:1 (2×30 mL) to give4-(3-Aminomethyl-phenyl)-4-hydroxy-piperidine-1-carboxylicacid-tert-butyl ester as a foam. This compound was used directly in thenext step.

To a stirred mixture of4-(3-Aminomethyl-phenyl)-4-hydroxy-piperidine-1-carboxylicacid-tert-butyl ester (0.30 g, 0.99 mmol), methylene chloride (10 mL)and water (10 mL) was added potassium carbonate (0.28 g, 2.02 mmol)followed by benzylchloroformate (0.34 g, 2.02 mmol). The reactionstirred overnight at room temperature. The reaction was extracted withmethylene chloride (3×30 mL). The organic extracts were combined, driedover sodium sulfate and evaporated to give a tan oil. Purification byflash chromatography 40% Ethyl acetate:Heptane yielded4-[3-(Benzyloxycarbonylamino-methyl)-phenyl]-4-hydroxy-piperidine-1-carboxylicacid-tert-butyl ester (0.40 g). ¹H NMR [(CDCl₃]: 7.45-7.18 (m, 9H), 5.15(s, 2H), 5.08 (br.s., 1H, NH), 4.40 (d, 2H), 4.15-3.93 (m, 2H),3.35-3.15 (m, 2H), 2.08-1.90 (m, 2H), 1.75-1.62 (m, 2H), 1.50 (s, 9H).

C.1-[4-(3-Aminomethyl-phenyl)-4-hydroxy-piperidin-1-yl]-1-(5-phenethyl-pyridin-3-yl)-methanone-ditrifluoroacetate

To a stirred solution of4-[3-(Benzyloxycarbonylamino-methyl)-phenyl]-4-hydroxy-piperidine-1-carboxylicacid-tert-butyl ester (0.38 g, 0.86 mmol) and methylene chloride (15 mL)at 0° C. was added trifluoroacetic acid (5 mL). The reaction was allowedto warm to room temperature, stirred one hour and was evaporated todryness to give [3-(4-(Hydroxy-piperidin-4-yl)-benzyl]-carbamic acidbenzyl ester which was used directly in the next step.

To a stirred solution of 5-phenethyl-pyridin-3-carboxylic acid (0.027 g,0.1 mmol) and DMF (10 mL) was added diisopropylethyl amine (0.014 g,0.11 mmol) followed by TBTU (0.0353 g, 0.11 mmol). This stirred for fiveminutes before adding a solution of[3-(4-(Hydroxy-piperidin-4-yl)-benzyl]-carbamic acid benzyl ester (0.045g, 0.1 mmol), DMF (2 mL) and Diisopropylethylamine (0.039 g, 0.3 mmol).The reaction stirred overnight at room temperature. The solvent wasremoved by evaporation and the remaining residue partitioned betweenethylacetate (50 mL) and saturated sodium bicarbonate (10 mL). Theorganic phase was separated, washed again with saturated sodiumbicarbonate (10 mL) and dried over magnesium sulfate. Evaporationfollowed by purification by flash chromatography (100% ethylacetate)gave(3-{4-Hydroxy-1-[-1-(5-phenethyl-pyridin-3-yl)-methanoyl]-piperidin-4-yl}-benzyl)-carbamicacid benzyl ester (0.030 g) as a clear oil. Hydrogenation with Methanol(10 mL), Acetic acid (1 mL) and a catalytic amount of 10% Palladium onCarbon overnight followed by filtration through celite gave the crudeproduct which was purified by HPLC as in Example 38 to give the titlecompound as an amorphous solid (9.1 mg). ¹H NMR [(CD₃)₂SO]: δ8.58-8.42(m, 2H), 8.15 (br.s., 3H, NH₃+), 7.73 (s, 1H), 7.63-7.51 (m, 2H), 7.40(t, 1H), 7.38-7.25 (m, 1H), 7.23-7.10 (m, 5H), 4.58-4.38 (m, 1H), 4.03(q, 2H), 3.60-3.10 (m, 3H), 3.05-2.86 (m, 4H), 2.06-1.80 (m, 2H),1.78-1.63 (m, 1H), 1.62-1.42 (m, 1H). MS(Ion spray): 416 (M⁺+1).

EXAMPLE 741-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(1-methyl-1H-indol-3-yl)-methanone-trifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 1-Methyl-1H-indole-3-carboxylic acid, there was prepared thetitle compound as an amorphous white solid. 1H NMR [CDCl₃]: 8.63 (br.s.,3H, NH₃ ⁺),7.60 (d, 1H), 7.51 (s, 1H), 7.41-7.18 (m, 5H), 7.15-7.05 (m,2H), 4.55-4.35 (m, 2H), 4.01 (br.s., 2H), 3.78 (s, 3H), 3.18-2.95 (m,2H), 2.80-2.61 (m, 1H), 1.85-1.45 (m, 4H). MS(Ion spray): 348 (M⁺+1).

EXAMPLE 751-(3-{1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-indol-1-yl)-ethanone-trifluoroacetate.

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 1-Acetyl-1H-indole-3-carboxylic acid, there was prepared thetitle compound as an amorphous white solid. 1H NMR [(CD₃)₂SO]: δ8.39 (d,1H), 8.21 (br.s., 3H, NH₃ ⁺), 8.13 (s, 1H), 7.70 (d, 1H), 7.68-7.25 (m,6H), 4.40 (br.s., 2H), 4.15-4.02 (m, 2H), 3.15-3.03 (m, 2H), 2.99-2.80(m, 1H), 2.71 (s, 3H), 1.95-1.76 (m, 2H), 1.74-1.55 (m, 2H). MS(Ionspray): 376 (M⁺+1).

EXAMPLE 761-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(5-methoxy-1-methyl-1H-indol-3-yl)-methanone-trifluoroacetate.

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 5-Methoxy-1-methyl-1H-indole-3-carboxylic acid, prepared as inWO 9522524, there was prepared the title compound as an amorphous whitesolid.

¹H NMR [(CD₃)₂SO]: δ8.13 (br.s., 3H, NH₃ ⁺), 7.71 (s, 1H), 7.51-7.23 (m,5H), 7.20 (s, 1H), 6.83 (dd, 1H), 4.53-4.40 (m, 2H), 4.13-3.95 (m, 2H),3.80 (s, 3H), 3.76 (s, 3H), 3.18-3.01 (m, 2H), 2.95-2.75 (m, 1H),1.95-1.76 (m, 2H), 1.75-1.52 (m, 2H). MS(Ion spray): 378 (M⁺+1).

EXAMPLE 771-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(2-trifluoromethyl-phenylethynyl)-phenyl]-methanonetrifluoroacetate

A. 4-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidine

As an alternative route, a one-pot cross coupling process was applied tothe preparation of the title compound. A solution of3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-bromobenzene (EXAMPLE 1A)(7.7 g, 20 mmol) in anhydrous DMF (60 ml) was treated with potassiumacetate (5.9 g, 60 mmol), bis(pinacolato)diboron (5 g, 20 mmol), and[1,1′-bis-(diphenylphosphino) ferroceno]-dichloropalladium(II)-dichloromethane complex (0.49 g, 0.60 mmol). This mixture wasstirred at 80° C. under an atmosphere of nitrogen for 4 hours, thenbenzyl1,2,3,6-tetrahydro-4-(trifluoromethylsulphonyloxy)-pyridine-1-carboxylate(EXAMPLE 1B) (9.2 g, crude, <25 mmol) was added, followed by aq Na₂CO₃(2M, 60 mL). The mixture was heated at 80° C. under an nitrogen foranother 2 hours and then concentrated. The cross coupling product (2.2g) was obtained after purification (as described in EXAMPLE 1B). Furtherreduction (as described in EXAMPLE 1B) yielded title compound.

B.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(2-trifluoromethyl-phenylethynyl)-phenyl]-methanonetrifluoroacetate

By proceeding in a similar manner to the coupling method described inEXAMPLE 5B, but using 2-iodobenzotrifluoride, and the deprotectionmethod described in EXAMPLE 38, the title compound was prepared as anamorphous off-white solid.¹H NMR [CD₃OD]: δ7.80-7.30 (m, 12H), 4.81 (br,1H), 4.10 (s, 2H), 3.87 (br 1H), 3.30 (br, 1H), 2.97 (m, 2H), 2.05-1.60(br, 4H). MS (Ion spray): 463 (M+1).

EXAMPLE 781-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(2-methyl-phenylethynyl)-phenyl]-methanonetrifluoroacetate

By proceeding in a similar manner to the coupling method described inEXAMPLE 5b, but using 2-iodotoluene, and the deprotection methoddescribed in EXAMPLE 38, the title compound was prepared as an amorphousoff-white solid. ¹H NMR [CD₃OD]: δ7.66-7.16 (m, 12H), 4.81 (br, 1H),4.11 (s, 2H), 3.87 (br 1H), 3.30 (br, 1H), 2.97 (m, 2H), 2.51 (s, 3H),2.05-1.60 (br, 4H). MS (Ion spray): 409 (M+1).

EXAMPLE 791-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(4-chloro-phenylethynyl)-phenyl]-methanonetrifluoroacetate

By proceeding in a similar manner to the coupling method described inEXAMPLE 5b, but using 1-chloro-4-iodobenzene, and the deprotectionmethod described in EXAMPLE 38, the title compound was prepared as anamorphous off-white solid. ¹H NMR [CD₃OD]: δ7.68-7.28 (m, 12H), 4.82(br, 11H), 4.11 (s, 2H), 3.87 (br 11H), 3.30 (br, I1H), 2.97 (m, 2H),2.05-1.60 (br, 4H). MS (Ion spray): 429 and 431 (M+1).

EXAMPLE 801-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(2-chloro-phenylethynyl)-phenyl]-methanonetrifluoroacetate

By proceeding in a similar manner to the coupling method described inEXAMPLE 5b, but using 1-chloro-2-iodobenzene, and the deprotectionmethod described in EXAMPLE 38, the title compound was prepared as anamorphous off-white solid. ¹H NMR [CD₃OD]: δ7.69-7.28 (m, 12H), 4.82(br, 1H), 4.11 (s, 2H), 3.87 (br 1H), 3.30 (br, 1H), 2.97 (m, 2H),2.05-1.60 (br, 4H). MS (Ion spray): 429 and 431 (M+1).

EXAMPLE 811-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(2-fluoro-phenylethynyl)-phenyl]-methanonetrifluoroacetate

By proceeding in a similar manner to the coupling method described inEXAMPLE 5b, but using 1-fluoro-2-iodobenzene, and the deprotectionmethod described in EXAMPLE 38, the title compound was prepared as anamorphous off-white solid. ¹H NMR [CD₃OD]: δ7.69-7.16 (m, 12H), 4.80(br, 1H), 4.10 (s, 2H), 3.84 (br 1H), 3.30 (br, 1H), 2.96 (m, 2H),2.05-1.60 (br, 4H). MS (Ion spray): 413 (M+1).

EXAMPLE 821-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(3-fluoro-phenylethynyl)-phenyl]-methanonetrifluoroacetate

By proceeding in a similar manner to the coupling method described inEXAMPLE 5b, but using 1-fluoro-3-iodobenzene, and the deprotectionmethod described in EXAMPLE 38, the title compound was prepared as anamorphous off-white solid. ¹H NMR [CD₃OD]: δ7.67-7.10 (m, 12H), 4.80(br, 1H), 4.10 (s, 2H), 3.85 (br 1H), 3.30 (br, 1H), 2.95 (m, 2H),2.05-1.60 (br, 4H). MS (Ion spray): 413 (M+1).

EXAMPLE 831-[4-(3-aminomethyl-phenyl)-piperidin-1-vii-1-[3-(4-fluoro-phenylethynyl)-phenyl]-methanonetrifluoroacetate

By proceeding in a similar manner to the coupling method described inEXAMPLE 5b, but using 1-fluoro-4-iodobenzene, and the deprotectionmethod described in EXAMPLE 38, the title compound was prepared as anamorphous off-white solid. ¹H NMR [CD₃OD]: δ7.64-7.10 (m, 12H), 4.80(br, 1H), 4.10 (s, 2H), 3.85 (br 1H), 3.30 (br, 1H), 2.97 (m, 2H),2.05-1.60 (br, 4H). MS (Ion spray): 413 (M+1).

EXAMPLE 841-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[2-(2-fluoro-phenyl)-ethyl]-phenyl}-methanonetrifluoroacetate

By proceeding in a similar manner to the reduction method described inEXAMPLE 9, and the deprotection method described in EXAMPLE 38, thetitle compound was prepared as an amorphous off-white solid. ¹H NMR[CD₃OD]: δ7.43-6.96 (m, 12H), 4.78 (br, 1H), 4.11 (s, 2H), 3.72 (br 1H),3.18 (br, 1H), 3.02-2.86 (m, 6H), 2.05-1.50 (br, 4H). MS (Ion spray):417 (M+1).

EXAMPLE 851-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[2-(3-fluoro-phenyl)-ethyl]-phenyl}-methanonetrifluoroacetate

By proceeding in a similar manner to the reduction method described inEXAMPLE 9, and the deprotection method described in EXAMPLE 38, thetitle compound was prepared as an amorphous off-white solid. ¹H NMR[CD₃OD]: δ7.43-6.80 (m, 12H), 4.78 (br, 1H), 4.11 (s, 2H), 3.70 (br 1H),3.18 (br, 1H), 3.02-2.85 (m, 6H), 2.05-1.50 (br, 4H). MS (Ion spray):417 (M+1).

EXAMPLE 861-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[2-(4-fluoro-phenyl)-ethyl]-phenyl-}-methanonetrifluoroacetate

By proceeding in a similar manner to the reduction method described inEXAMPLE 9, and the deprotection method described in EXAMPLE 38, thetitle compound was prepared as an amorphous off-white solid. ¹H NMR[CD₃OD]: δ7.43-6.88 (m, 12H), 4.78 (br, 1H), 4.10 (s, 2H), 3.69 (br 1H),3.18 (br, 1H), 3.00-2.85 (m, 6H), 2.05-1.50 (br, 4H). MS (Ion spray):417 (M+1).

EXAMPLE 871-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[2-(6-amino-pyridin-3-yl)ethynyl]-phenyl}-methanonetri-trifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using(6-tert-butoxycarbonylamino-pyridin-3-yl)ethynyl-pyridine-3-carboxylicacid (prepared according to the method described in EXAMPLE 7), thetitle compound was prepared as an amorphous off-white solid. ¹H NMR[CD₃OD]: δ8.82 (s, 1H), 8.66 (s, 1H), 8.17 (s, 1H), 8.07 (s, 1H), 8.02(d, 1H), 7.43-7.27 (m, 4H), 7.05 (d, 1H), 4.81 (br, 1H), 4.10 (s, 2H),3.79 (br 1H), 3.37 (br, 1H), 2.97 (m, 2H), 2.05-1.70 (br, 4H). MS (Ionspray): 412 (M+1).

EXAMPLE 881-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[2-(6-amino-pyridin-3-yl)-ethyl]-phenyl}-methanonetri-trifluoroacetate

By proceeding in a similar manner to the reduction method described inEXAMPLE 9, and the deprotection method described in EXAMPLE 38, thetitle compound was prepared as an amorphous off-white solid. ¹H NMR[CD₃OD]: δ8.60 (m, 2H), 7.94 (s, 1H), 7.89 (d, 1H), 7.61 (s, 1H),7.45-7.28 (m, 4H), 6.97 (d, 1H), 4.80 (br, 1H), 4.11 (s, 2H), 3.76 (br1H), 3.10-2.90 (m, 7H), 2.05-1.60 (br, 4H). MS (Ion spray): 416 (M+1).

EXAMPLE 891-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(6-chloro-thieno[3,2-b]thiophen-2-yl)-methanonetrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 6-chloro-thieno[3,2-b]thiophene-2-carboxylic acid, the titlecompound was prepared as an amorphous off-white solid. ¹H NMR [CD₃OD]:δ7.60 (s, 1H), 7.47 (s, 1H), 7.33-7.18 (m, 4H), 4.50 (br, 2H), 3.98 (s,2H), 3.12 (br, 2H), 2.86 (m, 1H), 1.85 (b, 2H), 1.67 (m, 2H). MS (Ionspray): 391 and 393 (M+1).

EXAMPLE 901-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(5-fluoro-thieno[3,2-b]thiophen-2-yl)-methanonetrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 5-fluoro-thieno[3,2-b]thiophene-2-carboxylic acid, the titlecompound was prepared as an amorphous off-white solid. ¹H NMR [CD₃OD]:δ7.65 (s, 1H), 7.44-7.17 (m, 4H), 7.03 (s, 1H), 4.60 (br, 2H), 4.12 (s,2H), 3.22 (br, 2H), 2.97 (m, 1H), 1.97 (b, 2H), 1.78 (m, 2H). MS (Ionspray): 375 (M+1).

EXAMPLE 911-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(5-methyl-thieno[3,2-b]thiophen-2-yl)-methanonetrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 5-methyl-thieno[3,2-b]thiophene-2-carboxylic acid, the titlecompound was prepared as an amorphous off-white solid. ¹H NMR [CD₃OD]:δ7.60 (s, 1H), 7.42-7.30 (m, 4H), 7.07 (s, 1H), 4.63 (br, 2H), 4.11 (s,2H), 3.21 (br, 2H), 2.97 (m, 1H), 2.60 (s, 3H), 1.96 (b, 2H), 1.78 (m,2H). MS (Ion spray): 371 (M+1).

EXAMPLE 921-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(5-chloro-thieno[3,2-b]thiophen-2-yl)-methanonetrifluoroacetate

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 5-chloro-thieno[3,2-b]thiophene-2-carboxylic acid, the titlecompound was prepared as an amorphous off-white solid. ¹H NMR [CD₃OD]:δ7.63 (s, 1H), 7.42-7.29 (m, 5H), 4.60 (br, 2H), 4.11 (s, 2H), 3.12 (br,2H), 2.97 (m, 1H), 1.97 (b, 2H), 1.78 (m, 2H). MS (Ion spray): 391

In a similar manner to the methods described above, the followingcompounds are prepared:

EXAMPLE 931-{4-[3-(1-aminoethyl)phenyl]-piperidin-1-yl}-1-(5-phenylethyl-pyridin-3-yl)-methanonedi-hydrochloride

A. [1-(3-Bromophenyl)ethyl]-carbamic acid tert-butyl ester

3-Bromoacetophenone oxime (23.4 mmol) was stirred in glacial acetic acid(l50 mL) at room temperature under nitrogen, and zinc dust (94 mmol)added portionwise. The reaction mixture was stirred at room temperaturefor 24 hours, filtered off the solids and concentrated the filtrate todryness. The residue was diluted with water, acidified to pH 5 with 1NHCl, and washed with ethyl acetate. The aqueous was basified with sodiumhydrogen carbonate, extracted into ethyl acetate, dried over magnesiumsulfate, and concentrated to dryness. The residue was dissolved indimethylformamide (30 mL) and triethylamine (36.9 mmol) added. To thissolution was added, dropwise, a solution of di-tert-butyldicarbonate(32.4 mmol) in DMF (10 mL). The reaction mixture was stirred at roomtemperature for 6 hours, and left standing for 24 hours beforeconcentrating to dryness. The residue was partitioned between water andethyl acetate, and the aqueous phase extracted with ethyl acetate. Thecombined organic phase was washed with brine, dried over magnesiumsulfate, and concentrated to dryness. The residue was purified by columnchromatography on silica gel with dichloromethane as eluent, to give[1-(3-bromophenyl)ethyl]-carbamic acid tert-butyl ester as a pale yellowoil which crystallized upon standing. MS(EI): 300 and 302 (M⁺+H).

B. 1-{4-[3-(1-Aminoethyl)phenyl]-piperidin-1-vii -1-(5-phenylethyl-pyridin-3-yl}-methanone di-hydrochloride

By proceeding in a manner similar to the method described in EXAMPLE17D, but using [1-(3-bromophenyl)ethyl]-carbamic acid tert-butyl esterin place of N-(tert-butoxycarbonyl)-3-bromo-4-fluorobenzylamine, therewas prepared[1-(3-{1-[1-(3-phenethyl-phenyl)-methanoyl]-1,2,3,6-tetrahydro-pyridin-4-yl}-phenyl)-ethyl]-carbamicacid tert-butyl ester. This material was subjected to the sameconditions as described in EXAMPLE 2A, but using[1-(3-{1-[1-(3-phenethyl-phenyl)-methanoyl]-1,2,3,6-tetrahydro-pyridin-4-yl}-phenyl)-ethyl]-carbamicacid tert-butyl ester in place of 5-phenylethynylpyridine-3-carboxylicacid. The crude product from this reaction was purified by columnchromatography on silica gel, before being subjected to the sameconditions as described in EXAMPLE 1D, but using[1-(3-{1-[1-(3-phenethylphenyl)-methanoyl]-piperidin-4-yl}phenyl)ethyl]carbamicacid tert-butyl ester in place of3-[1-(5-phenylethynylpyridine-3-carbonyl)piperidin-4-yl]benzonitrile.1-{4-[3-(1-Aminoethyl)phenyl]-piperidin-1-yl}-1-(5-phenylethyl-pyridin-3-yl)-methanonedi-hydrochloride was isolated as a pale yellow solid. MS(EI): 414(M⁺+H).

EXAMPLE 941-[4-(5-aminomethyl-3-hydroxyphenyl)-piperidin-1-yl]-1-(5-phenylethyl-pyridin-3-yl)-methanonedi-hydrochloride

A.3-Bromo-N,N-(bis-tert-butoxycarbonyl)-5-(tert-butyldimethylsilyloxy)benzylamine(3-Bromo-5-methyl-phenoxy)-tert-butyldimethylsilane (3.32 mmol)[prepared according to the procedure of J. E. Baldwin et al,Tetrahedron, 1991, 47(29), 5603], N-bromosuccinimide (3.65 mmol), andbenzoyl peroxide (0.332 mmol) were dissolved in dichloromethane (10 ml)and the reaction mixture irradiated for 4 hours. Diluted withdichloromethane and washed with water, dried over magnesium sulfate andconcentrated to dryness. The crude material was purified by columnchromatography on silica gel with 10% ethyl acetate/cyclohexane to give(3-bromo-5-bromomethyl-phenoxy)-tert-butyldimethylsilane as a colorlessoil. This material was subjected to the conditions described in thefirst part of EXAMPLE 1A, but using(3-bromo-5-bromomethyl-phenoxy)-tert-butyldimethylsilane in place of3-bromobenzylbromide, to give3-bromo-N,N-(bis-tert-butoxycarbonyl)-5-(tert-butyldimethylsilyloxy)benzylamineas a colorless oil. MS (EI) 516 and 518 (M⁺+H).

B.1-(5-Phenylethynylpyridine-3-carbonyl)-4-(pinacolatoboronyl)-1,2,3,6-tetrahydropyridine

By proceeding in a manner similar to the method described in EXAMPLE17B, but using 5-phenylethynylpyridine-3-carboxylic acid in place of5-phenethylpyridine-3-carboxylic acid , there was prepared1-(5-phenylethynylpyridine-3-carbonyl)-4-(pinacolatoboronyl)-1,2,3,6-tetrahydropyridineas a pale yellow solid. MS (EI) 415 (M⁺+H).

C.1-{4-[3-(N,N-bis-tert-Butoxycarbonyl)aminomethyl-5-hydroxyphenyl]-3,6-dihydro-2H-pyridin-1-yl}-1-(5-phenylethynylpyridin-3-yl)methanone

By proceeding in a manner similar to the method described in EXAMPLE17D, but using3-bromo-N,N-(bis-tert-butoxycarbonyl)-5-(tert-butyldimethylsilyloxy)benzylaminein place of N-(tert-butoxycarbonyl)-3-bromo-4-fluorobenzylamine and1-(5-phenylethynylpyridine-3-carbonyl)-4-(pinacolatoboronyl)-1,2,3,6-tetrahydropyridinein place of1-(5-phenylethylpyridine-3-carbonyl)-4-(pinacolatoboronyl)-1,2,3,6-tetrahydropyridine,there was prepared1-{4-[3-(N,N-bis-tert-Butoxycarbonyl)aminomethyl-5-hydroxyphenyl]-3,6-dihydro-2H-pyridin-1-yl}-1-(5-phenylethynylpyridin-3-yl)methanoneas a pale brown solid. MS (EI) 610 (M⁺+H). The tert-butyl-dimethylsilylmoiety had unexpectedly been removed during this procedure.

D.1-[4-(5-Aminomethyl-3-hydroxyphenyl)-piperidin-1-yl]-1-(5-phenylethyl-pyridin-3-yl)-methanonedi-hydrochloride

By proceeding in a manner similar to the method described in EXAMPLE 2A,but using1-{4-[3-(N,N-bis-tert-butoxycarbonyl)aminomethyl-5-hydroxyphenyl]-3,6-dihydro-2H-pyridin-1-yl}-1-(5-phenylethynylpyridin-3-yl)methanonein place of 5-phenylethynylpyridine-3-carboxylic acid, there wasprepared1-{4-[3-(N,N-bis-tert-butoxycarbonyl)aminomethyl-5-hydroxy-phenylpiperidin-yl}-1-(5-phenethylpyridin-3-yl)methanone.The crude product from this reaction was purified by columnchromatography on silica gel, before being subjected to the sameconditions as described in EXAMPLE 1D, but using1-{4-[3-(N,N-bis-tert-butoxycarbonyl)aminomethyl-5-hydroxy-phenyl]piperidin-1-yl}-1-(5-phenethylpyridin-3-yl)methanonein place of3-[1-(5-phenylethynylpyridine-3-carbonyl)piperidin-4-yl]benzonitrile.1-[4-(5-Aminomethyl-3-hydroxyphenyl)-piperidin-1-yl]-1-(5-phenylethyl-pyridin-3-yl)-methanonedi-hydrochloride was isolated as a pale yellow solid. MS(EI): 416(M⁺+H).

EXAMPLE 951-[4-(5-aminomethyl-2-hydroxyphenyl)-piperidin-1-yl]-1-(5-phenylethyl-pyridin-3-yl)-methanonedi-hydrochloride

A. 4-Benzyloxy-3-bromobenzyl carbamic acid tert-butyl ester

3-Bromo-4-flurobenzonitrile (3.00 g, 15 mmol), benzyl alcohol (1.71 ml,16.5 mmol) and THF (40 ml) are combined and treated with 60% sodiumhydride in oil (0.66 g, 16.5 mmol). The reaction mixture is heated toreflux under nitrogen for 3 hours. Aqueous workup and chromatographicpurification (cyclohexane:dichloromethane, 3:1) yields4-benzyloxy-3-bromobenzonitrile as a white solid (3.88 g, 13.5 mmol). Aportion of this material (2.64 g, 9.16 mmol) in THF (25 ml) is treatedwith a 1 M solution of borane in THF (18.3 ml, 18.3 mmol). After theexotherm subsides the reaction is refluxed a couple of days undernitrogen. The excess borane is destroyed by the addition of methanol and4-benzyloxy-3-bromobenzylamine is precipitated as the hydrochloride salt(1.58 g, 4.8 mmol). This material is suspended in dichloromethane (30ml) and treated successively with triethyl amine (1.68 ml, 12.02 mmol)and di-tert-butyl dicarbonate (1.26 g, 5.77 mmol). The reaction mixtureis stirred under nitrogen four hours; aqueous workup and chromatographicpurification (ethyl acetate:cyclohexane, 3:7) yields the title compoundas a white solid (1.69 g, 4.3 mmol). MS(EI): 394(M⁺).

B.4-Benzyloxy-3-{1-[1-(5-phenylethylpyridin-3-yl)methanoyl]-1,2,3,6-tetrahydropyridin-4-yl}-benzylcarbamic acid tert-butyl ester

1-(5-Phenylethylpyridine-3-carbonyl)-4-(pinacolatoboronyl)-1,2,3,6-tetrahyropyridine(0.628 g, 1.5 mmol) as prepared in EXAMPLE 17B,4-benzyloxy-3-bromobenzyl carbamic acid tert-butyl ester (0.62 g, 1.58mmol), dichlorobis(triphenylphosphine)palladium (II) (0.074, 0.08 mmol),potassium carbonate (0.622 g, 4.5 mmol) and DMF (15 mL) are heated to80° C. under nitrogen for 3 hours. The DMF is removed in vacuo, theresidue is subjected to an aqueous workup and the organic residue ispurified by chromatography to give a gray foam (0.45 g, 0.75 mmol).

C.3-Hydroxy-2-{1-[1-(5-phenylethylpyridin-3-yl)methanoyl]-piperidin-4-yl}-benzylcarbamic acid tert-butyl ester

4-Benzyloxy-3-{1-[1-(5-phenylethylpyridin-3-yl)methanoyl]-1,2,3,6-tetrahydropyridin-4-yl}-benzylcarbamic acid tert-butyl ester (0.34 g, 0.56 mmol) is hydrogenolyzedwith hydrogen gas and 10% P/C to give the title compound as a white foam(0.27 g, 0.52 mmol). MS(EI): 515(M⁺).

D.1-[4-(5-Aminomethyl-2-hydroxyphenyl)-piperidin-1-yl]-1-(5-phenylethyl-pyridin-3-yl)-methanonedi-hydrochloride

3-Hydroxy-2-1-[1-(5-phenylethylpyridin-3-yl)methanoyl]-piperidin-4-yl]-benzylcarbamic acid tert-butyl ester (0.09 g, 0.175 mmol) is converted to thetitle compound (0.053 g, 0.11 mmol) by the procedure described inEXAMPLE 5C. MS(EI): 416(M⁺+H).

EXAMPLE 961-[4-(5-aminomethyl-2-benzyloxyphenyl)-3,6-dihydro-2H-pyridin-1-yl]-1-(5-phenylethyl-pyridin-3-yl)-methanonedi-hydrochloride

4-Benzyloxy-3-{1-[1-(5-phenylethylpyridin-3-yl)methanoyl]-1,2,3,6-tetrahydropyridin-4-yl}-benzylcarbamic acid tert-butyl ester (0.11 g, 0.184 mmol) is converted to thetitle compound (0.080 g, 0.15 mmol) by the procedure described inEXAMPLE 5C. MS(EI): 504(M⁺+H).

EXAMPLE 971-[4-(3-aminomethylphenyl)-piperidin-1-yl]-1-(4-phenylethyl-phenyl)-methanonehydrochloride

A. 4-Phenylethynylbenzoic acid.

4-Phenylethynylbenzaldehylde (1.01 g, 4.85 mmol) is added to asuspension of silver oxide (0.56 g, 2.43 mmol) in water (15 ml) andsodium hydroxide (0.97 g, 24.3 mmol). The reaction mixture is heated to90° C. for 1.5 hours cooled and acidified. The aqueous mixture isextracted with ethyl acetate and the organic layer is concentrated. Theresultant solid is partitioned between ether and 0.1 M sodium hydroxidesolution. The aqueous layer is acidified and the precipitated titlecompound (0.55 g, 2.5 mmol) is collected. M.P. 224-225° C.; MS(EI):222(M⁺)

B.1-[4-(3-Aminomethylphenyl)-piperidin-1-yl]-1-(4-phenylethyl-phenyl)-methanonehydrochloride

By proceeding in similar manner to the method described in EXAMPLE 1Cbut using 4-phenylethynyl benzoic acid,N,N-bis-(tert-butoxycarbonyl)-3-[1-(4-phenylethynyl-benzoyl)-piperidin-4-yl]-benzylaminewas prepared. The title compound is subsequently prepared by applying insequence the methods described in EXAMPLE 9. MS(EI): 399(M⁺+H).

EXAMPLE 981-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[2-(2-hydroxy-phenyl)-ethyl]-phenyl}-methanonehydrochloride

By proceeding in a similar manner to the method described in EXAMPLE 10but usingN,N-bis-(tert-butoxycarbonyl)-3-{1-[3-(2-hydroxyphenyl)ethynyl-benzoyl]-piperidin-4-yl}-benzylamine,which was prepared in a similar manner to the method described inEXAMPLE 6a but using 2-iodophenol, there was prepared the title compoundas a white amorphous solid. MS(EI): 415 (M+H).

EXAMPLE 991-[4-(5-aminomethyl-2-hydroxymethylphenyl)-3,6-dihydro-2H-pyridin-1-yl]-1-(5-phenylethyl-pyridin-3-yl)-methanone

A. Acetic acid 4-(N,N-bis-tert-butoxycarbonyl)aminomethyl-2-bromobenzylester

2-Bromo-4-(bromomethyl)benzylbromide (2.91 mmol) [prepared according tothe procedure of Bridger et al, J. Med. Chem. 1995, 38(2), 366] anddi-tert-butyliminodicarboxylate (2.91 mmol) were dissolved intetrahydrofuran (10 mL), and sodium hydride (60% in mineral oil, 2.91mmol) added at room temperature under argon. The reaction mixture wasstirred at room temperature for 4 days, quenched with saturated aqueousammonium chloride, extracted into ethyl acetate, washed with brine,dried over magnesium sulfate, and concentrated to dryness. The cruderesidue was purified by column chromatography on silica gel withcyclohexane:ethyl acetate=9:1.3-bromo-4-bromomethyl-(N,N-bis-tert-butoxycarbonyl)benzylamine wasisolated as a white solid. A portion of3-bromo-4-bromomethyl-(N,N-bis-tert-butoxycarbonyl)benzylamine(1.88mmol) was dissolved in acetonitrile (15 mL), and to this was addedpotassium acetate (3.7 mmol) and 18-crown-6 (0.095 mmol). The reactionmixture was stirred at room temperature for 16 hours, concentrated todryness, extracted into ethyl acetate, washed with brine, dried overmagnesium sulfate, and concentrated to dryness. Purification was carriedout by column chromatography on silica gel with diethylether:cyclohexane=1:1. Acetic acid4-(N,N-bis-tert-butoxycarbonyl)aminomethyl-2-bromobenzyl ester wasisolated as a colorless solid. MS (EI) 458 and 460 (M⁺+H).

B.1-{4-[5-(N,N-bis-tert-Butoxycarbonyl)aminomethyl-2-acetoxymethylphenyl]-3,6-dihydro-2H-pyridin-1-yl}-1-(5-phenethylpyridin-3-yl)methanone

By proceeding in a manner similar to the method described in EXAMPLE17D, but using acetic acid4-(N,N-bis-tert-butoxycarbonyl)aminomethyl-2-bromobenzyl ester in placeof N-(tert-butoxycarbonyl)-3-bromo-4-fluorobenzylamine, there wasprepared1-{4-[5-(N,N-bis-tert-butoxycarbonyl)aminomethyl-2-acetoxymethylphenyl]-3,6-dihydro-2H-pyridin-1-yl}-1-(5-phenethylpyridin-3-yl)methanone.MS (EI) 670 (M⁺+H).

C.1-[4-(5-Aminomethyl-2-hydroxymethylphenyl)-3,6-dihydro-2H-pyridin-1-yl]-1-(5-phenylethyl-pyridin-3-yl)-methanone

1-{4-[5-(N,N-bis-tert-Butoxycarbonyl)aminomethyl-2-acetoxymethylphenyl]-3,6-dihydro-2H-pyridin-1-yl}-1-(5-phenethylpyridin-3-yl)methanone(0.3 mmol) was dissolved in methanol (10 mL) and cooled at 0° C. whilstadding potassium carbonate (0.1 mmol). Left at room temperature for 16hours, concentrated to dryness and used crude residue directly in thenext step. By proceeding in a manner similar to the method described inEXAMPLE 1D, but using1-{4-[5-(N,N-bis-tert-butoxycarbonyl)aminomethyl-2-hydroxymethylphenyl-3,6-dihydro-2H-pyridin-1-yl}-1-(5-phenethylpyridin-3-yl)methanonein place of3-[1-(5-phenylethynylpyridine-3-carbonyl)piperidin-4-yl]benzonitrile,there was prepared1-[4-(5-aminomethyl-2-hydroxymethylphenyl)-3,6-dihydro-2H-pyridin-1-yl]-1-(5-phenylethyl-pyridin-3-yl)-methanoneas a pale yellow solid. MS(EI): 428 (M⁺+H).

EXAMPLE 1001-[4-(5-aminomethyl-thiophen-2-yl)-piperidin-1-yl]-(5-phenylethyl-pyridin-3-yl)-methanonedi-hydrochloride

A. 2-N,N-Bis-(tert-butoxycarbonyl)aminomethyl]-4-bromo-thiophene

By proceeding in a similar manner to the method described in EXAMPLE 1Abut using 4-bromo-2-bromomethyl-thiophene, which was simply preparedfrom reduction of 4-bromo-thiophene-2-carbaldehyde and subsequentbromonation of the alcohol, there was prepared the title compound.

B.1-[4-(5-Aminomethyl-thiophen-2-yl)-piperidin-1-yl]-(5-phenylethyl-pyridin-3-yl)-methanonedi-hydrochloride

By proceeding in a similar manner to the method described in EXAMPLE 93but using2-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-4-bromo-thiophene, therewas prepared the title compound as a white amorphous solid. MS(EI):406(M+H).

EXAMPLE 101[4-(5-aminomethyl-pyridin-3-yl)-piperidin-1-yl]-1-(5-phenylethyl-pyridin-3-yl)-methanonetri-hydrochloride

A. 3-Bromo-5-(N,N-bis-tert-butoxycarbonyl)aminomethylpyridine

3-Bromo-5-hydroxymethylpyridine (16.1 mmol) [prepared according to theprocedure of Ashimori et al, Chem. Pharm. Bull. 1990, 38(9), 2446] andpyridine (32.3 mmol) were dissolved in acetonitrile (32 mL) and cooledto 0° C. Dibromotriphenylphosphorane (20.9 mmol) added, and leftreaction mixture to warm to room temperature in stoppered flask for 4hours. The crude reaction mixture was purified by column chromatographydirectly on silica gel with diethyl ether:cyclohexane=1:1.3-Bromo-5-bromomethylpyridine was isolated as a pale brown solid.3-Bromo-5-bromomethylpyridine (7.7 mmol) anddi-tert-butyliminodicarboxylate (10 mmol) were dissolved intetrahydrofuran (20 mL), and sodium hydride (60% in mineral oil, 10mmol) added at room temperature under argon. The reaction mixture wasstirred at room temperature for 16 hours, quenched with saturatedaqueous ammonium chloride, extracted into ethyl acetate, washed withbrine, dried over magnesium sulfate, and concentrated to dryness. Thecrude residue was purified by column chromatography on silica gel withcyclohexane:diethyl ether=2:1.3-bromo-5-(N,N-bis-tert-butoxycarbonyl)aminomethylpyridine was isolatedas a pale yellow solid. MS (EI) 387 and 389 (M⁺+H).

B.[4-(5-Aminomethyl-pyridin-3-yl)-piperidin-1-yl]-1-(5-phenylethyl-pyridin-3-yl)-methanonetri-hydrochloride

By proceeding in a manner similar to the method described in EXAMPLE17D, but using3-bromo-5-(N,N-bis-tert-butoxycarbonyl)aminomethylpyridine in place ofN-(tert-butoxycarbonyl)-3-bromo-4-fluorobenzylamine and1-(5-phenylethynylpyridine-3-carbonyl)-4-(pinacolatoboronyl)-1,2,3,6-tetrahydropyridinein place of1-(5-phenylethylpyridine-3-carbonyl)-4-(pinacolatoboronyl)-1,2,3,6-tetrahydropyridine,there was prepared1-[5-(N,N-bis-tert-butoxycarbonyl)aminomethyl-3′,6′-dihydro-2′H-[3,4′]bipyridinyl-1′-yl]-1-(5-phenylethynylpyridin-3-yl)methanone.This material was subjected to the same conditions as described inEXAMPLE 2A, but using1-[5-(N,N-bis-tert-butoxycarbonyl)aminomethyl-3′,6′-dihydro-2′H-[3,4′]bipyridinyl-1′-yl]-1-(5-phenylethynylpyridin-3-yl)methanonein place of 5-phenylethynylpyridine-3-carboxylic acid. The crude productfrom this reaction was purified by column chromatography on silica gel,before being subjected to the same conditions as described in EXAMPLE1D, but using{4-[5-(N,N-bis-tert-butoxycarbonyl)aminomethylpyridin-3-yl]-piperidin-1-yl}-1-(5-phenylethyl-pyridin-3-yl)-methanonein place of3-[1-(5-phenylethynylpyridine-3-carbonyl)piperidin-4-yl]benzonitrile.[4-(5-Aminomethyl-pyridin-3-yl)-piperidin-1-yl]-1-(5-phenylethyl-pyridin-3-yl)-methanonetri-hydrochloride was isolated as a pale yellow solid. MS(EI): 401(M⁺+H).

EXAMPLE 1021-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(1-ethyl-1H-indol-3-yl)-methanone-trifluoroacetate.

A. 1-Ethyl-1H-indole-3-carboxylic acid methyl ester.

A flask was charged with 1H-indole-3-carboxylic acid methyl ester (2 g,11.41 mmol) and iodoethane (4.4 g, 28.5 mmol) in dry THF (25 mL). Themixture was stirred in a water bath and a 60% dispersion of sodiumhydride (0.68 g, 17.12 mmol) in mineral oil was added in portions over 5minutes. The reaction stirred for 48 hours and was quenched by carefuladdition of water. The mixture was extracted with dichloromethane (2×100mL), dried over sodium sulfate and evaporated under reduced pressure.The crude product was purified by silica flash chromatography (10% ethylacetate/heptane) to give 1-ethyl-1H-indole-3-carboxylic acid methylester (1.8 g). ¹H NMR [CDCl₃]: 8.22-8.15 (m, 1H), 7.87 (s, 1H),7.42-7.33 (m, 1H), 7.31-7.25 (m, 2H), 4.22 (q, 2H), 3.92 (s, 3H), 1.52(t, 3H).

B. 1-Ethyl-1H-indole-3-carboxylic acid.

A solution of 1-ethyl-1H-indole-3-carboxylic acid methyl ester (1.8 g,8.8 mmol) was stirred in a 1:1 mixture of THF:MeOH (40 mL), and to thiswas added 2N NaOH (20 mL). The reaction was heated at reflux for 4hours. The reaction mixture was partially evaporated to remove the THF,MeOH and the remaining material diluted with water (20 mL) and acidifiedto pH=2 with 1N HCl. The mixture was extracted with dichloromethane (100mL), dried over sodium sulfate and evaporated under reduced pressure togive the title compound as a white solid, which was used directly in thenext step.

C.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(1-ethyl-1H-indol-3-yl)-methanone-trifluoroacetate.

By proceeding in a similar manner to the method described in EXAMPLE 38,but using 1-ethyl-1H-indole-3-carboxylic acid, there was prepared thetitle compound as an amorphous white solid. ¹H NMR [CD₃OD]: δ7.75-7.63(m, 2H), 7.52 (d, 1H), 7.43-7.36 (m, 3H), 7.35-7.15 (m, 3H), 4.63-4.51(m, 2H), 4.30 (q, 2H), 4.11 (s, 2H), 3.30-3.13 (m, 2H), 3.03-2.85 (m,1H), 2.00-1.86 (m, 2H), 1.85-1.68 (m, 2H), 1.49 (t, 3H). MS (ion spray):362 (M⁺+1).

A. 4-Hydroxy-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-benzylester 3-ethyl ester

To a solution of ethyl 4-piperidone-3-carboxylate hydrochloride (5 g,24.05 mmol) in THF (70 mL) and water (35 mL) at 0° C., was addedtriethylamine (8.7 mL, 62.5 mmol), followed byN-(benzyloxycarbonyloxy)succinimide (7.79 g, 31.27 mmol). The reactionmixture was stirred and allowed to warm to room temperature. After 3hours the reaction mixture was diluted with water (50 mL) and ethylacetate (100 mL) added. The aqueous phase was extracted into ethylacetate (2×100 mL). The organic phases were combined, washed with brine(50 mL), dried (MgSO₄), and the solvent removed in vacuo. The crudeproduct was purified by column chromatography on silica gel (eluent,ethyl acetate:pentane=1:5) to give4-hydroxy-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-benzyl ester3-ethyl ester as a colorless oil (7.26 g, 94%). MS (EI) 305 (M⁺).

B. 4-Trifluoromethanesulfonyloxy-5,6-dihydro-2H-pyridine-13-dicarboxylic acid 1-benzyl ester 3-ethyl ester

4-Hydroxy-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-benzyl ester3-ethyl ester (15.94 g, 52.5 mmol) was dissolved in anhydrous THF (150mL) under nitrogen and cooled at −78° C. during the addition of sodiumbis(trimethylsilyl)amide (1M in THF; 68 mL, 68 mmol) via cannula. Afterstirring for 30 minutes at this temperature a solution ofN-phenyltrifluoromethanesulfonimide (22.42 g, 62.8 mmol) in THF (230 mL)was added dropwise via cannula. The reaction mixture was stirred at thistemperature for 10 minutes before warming to 0° C. and stirring for 2hours. After 48 h the reaction mixture was quenched with water,extracted into DCM, dried (MgSO₄) and concentrated in vacuo. The crudeproduct was purified by flash column chromatography on silica gel(eluent; ethyl acetate:pentane =4:1) to give4-trifluoromethanesulfonyloxy-5,6-dihydro-2H-pyridine-1,3-dicarboxylicacid 1-benzyl ester 3-ethyl ester as colorless oil (18.59 g, 81%). Thismaterial decomposed to a deep red material upon standing so was storedunder nitrogen at 0° C. in the dark. MS (EI) 437 (M⁺).

C.4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydro-2H-pyridine-1,3-dicarboxylicacid 1-benzyl ester 3-ethyl ester

4-Trifluoromethanesulfonyloxy-5,6-dihydro-2H-pyridine-1,3-dicarboxylicacid 1-benzyl ester 3-ethyl ester (200 mg, 0.458 mmol) was dissolved inanhydrous dioxane (6 mL), and added dropwise, via cannula, to a mixtureof potassium acetate (135 mg, 1.374 mmol),1,1′-bis(diphenylphosphino)ferrocene (8 mg, 0.014 mmol),[1,1′-bis(diphenylphosphino)ferroceno]dichloropalladium-dichloromethanecomplex (10 mg, 0.014 mmol), and bis-pinnacolato diborane (116 mg, 0.458mmol), under nitrogen. The mixture was heated at 80° C. overnight,cooled to room temperature and partitioned between DCM and water. Theaqueous phase was extracted with DCM, and the organic phases combinedand dried (MgSO₄). Th crude product was purified by flash columnchromatography on silica gel (eluent; pentane:ethyl acetate=5:1) toafford4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydro-2H-pyridine-1,3-dicarboxylicacid 1-benzyl ester 3-ethyl ester as a colorless oil (94 mg, 50%). MS(EI) 415 (M⁺).

D.4-{3-[(N,N-Bis-tert-butoxycarbonyl)aminomethyl]phenyl}-5,6-dihydro-2H-pyridine-1,3-dicarboxylicacid 1-benzyl ester 3-ethyl ester

A solution of 3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]bromobenzene(3.51 g, 9.1 mmol) [prepared by the method in Example 1A] and4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydro-2H-pyridine-1,3-dicarboxylicacid 1-benzyl ester 3-ethyl ester (3.6 g, 8.67 mmol) in DMF (120 mL)were added, via cannula, to a mixture of[1,1′-bis(diphenylphosphino)ferroceno]dichloropalladium-dichloromethanecomplex (425 mg, 0.52 mmol) and potassium carbonate (3.59 g, 26 mmol)under nitrogen. The reaction mixture was heated at 80° C. overnight,concentrated to dryness in vacuo, and the residue partitioned betweenDCM and water. The aqueous phase was extracted with DCM, the organicphases combined, washed with brine, and dried (MgSO₄). The crudematerial was purified by column chromatography on silica gel (eluent;pentane: ethyl acetate=6:1) to give4-{3-[(N,N-bis-tert-butoxycarbonyl)aminomethyl]phenyl}-5,6-dihydro-2H-pyridine-1,3-dicarboxylicacid 1-benzyl ester 3-ethyl ester as a colorless oil (2.27 g, 44%). MS(EI) 594 (M⁺).

E. (3S, 4S) and (3R,4R)4-{3-[(N,N-Bis-tert-butoxycarbonyl)aminomethyl]phenyl}-piperidine-3-carboxylicacid ethyl ester

Solid carbon dioxide (1 g) was added to a solution of4-{3-[(N,N-bis-tert-butoxycarbonyl)aminomethyl]phenyl)-5,6-dihydro-2H-pyridine-1,3-dicarboxylicacid 1-benzyl ester 3-ethyl ester (2.07 g, 3.48 mmol) in IMS (20 mL).10% palladium on carbon (200 mg) was added and the reaction mixturestirred at room temperature, under an atmosphere of hydrogen, for 4hours. The palladium on carbon was filtered off through celite to give a1:1 mixture of (3S, 4S) and (3R,4R)4-{3-[(N,N-Bis-tert-butoxycarbonyl)aminomethyl]phenyl-piperidine-3-carboxylicacid ethyl ester as a pale grey/brown oil (1.35 g, 84%), which was pureenough for use in the subsequent reaction. MS (EI) 462 (M⁺).

F. (3S,4S) and(3R,4R)-4-{3-[(Bis-tert-butoxycarbonyl)aminomethyl]phenyl}-1-(5-phenethylpyridine-3-carbonyl)piperidine-3-carboxylicacid ethyl ester

By proceeding in a similar manner to the method described in EXAMPLE 2B,but using a 1:1 mixture of (3S, 4S) and (3R,4R)4-{3-[(N,N-Bis-tert-butoxycarbonyl)aminomethyl]phenyl}-piperidine-3-carboxylicacid ethyl ester instead of4-{3-[N,N-bis(tert-butoxycarbonyl)aminomethyl]phenyl}piperidine, therewas prepared a 1:1 mixture of (3S,4S) and(3R,4R)-4-{3-[(Bis-tert-butoxycarbonyl)aminomethyl]phenyl}-1-(5-phenethylpyridine-3-carbonyl)piperidine-3-carboxylicacid ethyl ester as a colorless glassy solid (414 mg, 0.62 mmol). MS(EI) 671 (M⁺).

G. (3S,4S) and (3R,4R)-4-(3-Aminomethyl-phenyl)-1-(5-phenethyl-pyridine-3-carbonyl)-piperidine-3-carboxylicacid ethyl ester dihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE 1D,but using a 1:1 mixture of (3S,4S) and(3R,4R)-4-{3-[(Bis-tert-butoxycarbonyl)aminomethyl]phenyl}-1-(5-phenethylpyridine-3-carbonyl)piperidine-3-carboxylicacid ethyl ester instead ofN,N-bis-(tert-butoxycarbonyl)-3-[1-(5-phenylethynylpyridine-3-carbonyl)piperidin-4-yl]benzylamine,there was prepared a 1:1 mixture of (3S,4S) and (3R,4R)-4-(3-Aminomethyl-phenyl)-1-(5-phenethyl-pyridine-3-carbonyl)-piperidine-3-carboxylicacid ethyl ester dihydrochloride as a white solid. MS (EI) 471 (M⁺).

EXAMPLE 104 (3R,4S) and (3S,4R)-4-(3-aminomethyl-phenyl)-1-(5-phenethyl-pyridine-3-carbonyl)-piperidine-3-carboxylicacid ethyl ester dihydrochloride

A. (3R,4S) and(3S,4R)-4-{3-[(tert-Butoxycarbonyl)aminomethyl]phenyl}-1-(5-phenethylpyridine-3-carbonyl)-piperidine-3-carboxylicacid ethyl ester

Sodium hydride (10 mg, 60% in mineral oil, 0.25 mmol) was added toethanol (10 mL), and after the effervescence had subsided a 1:1 mixtureof (3S,4S) and(3R,4R)-4-{3-[(bis-tert-butoxycarbonyl)aminomethyl]phenyl}-1-(5-phenethylpyridine-3-carbonyl)piperidine-3-carboxylicacid ethyl ester (100 mg) was added at room temperature. After 1 hourthe solvent was removed in vacuo, and the residue partitioned betweenDCM and water. The aqueous phase was extracted with DCM, the combinedorganic phase washed with brine and dried (MgSO₄). The crude materialwas purified by column chromatography on silica gel (eluent;DCM:MeOH=10:1) to give a 1:1 mixture of (3R,4S) and(3S,4R)-4-{3-[(tert-butoxycarbonyl)aminomethyl]phenyl}-1-(5-phenethylpyridine-3-carbonyl)-piperidine-3-carboxylicacid ethyl ester as a pale yellow glassy solid (43 mg, 51%). MS (EI) 571(M⁺).

B. (3R,4S) and (3S,4R)-4-(3-Aminomethyl-phenyl)-1-(5-phenethyl-pyridine-3-carbonyl)-piperidine-3-carboxylicacid ethyl ester dihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE 1D,but using a 1:1 mixture of (3R,4S) and(3S,4R)-4-{3-[(tert-butoxycarbonyl)aminomethyl]phenyl}-1-(5-phenethylpyridine-3-carbonyl)-piperidine-3-carboxylicacid ethyl ester instead ofN,N-bis-(tert-butoxycarbonyl)-3-[1-(5-phenylethynylpyridine-3-carbonyl)piperidin-4-yl]benzylamine,there was prepared a 1:1 mixture of (3R,4S) and (3S,4R)-4-(3-aminomethyl-phenyl)-1-(5-phenethyl-pyridine-3-carbonyl)-piperidine-3-carboxylicacid ethyl ester dihydrochloride as a white solid. MS (EI) 471 (M⁺).

EXAMPLE 1051-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[5-(4-bromo-2-fluoro-benzylamino)-pyridin-3-yl]-methanonetrihydrochloride

A. 5-tert-Butoxycarbonylamino-nicotinic acid

To a solution of diethyl 3,5-pyridinedicarboxylate [prepared accordingto the procedure of J. C. Speelman and R. M. Kellogg, J. Org. Chem.,1990, 55 (2), pages 647-653; 64.19 g, 0.248 mol] in ethanol (650 mL)were added KOH pellets (14.56 g, 0.260 mol). The reaction mixture wasstirred overnight at ambient temperature. Evaporation of solventafforded a white solid that was rinsed with dichloromethane, and thendissolved in water. The aqueous solution was extracted with ether, andthen acidified to pH 3. The resultant white precipitate was collected byfiltration and dried to afford pyridine-3,5-dicarboxylic acid monomethylester (33.70 g). A portion of this material (10.00 g, 51.3 mmol) wasdissolved in dry tert-butanol (300 mL) and treated sequentially withtriethylamine (7.85 mL, 56.4 mmol) and diphenyl phosphoryl azide (11.5mL, 53.4 mmol). The mixture was refluxed for 90 minutes, and thenstirred at ambient temperature overnight. Solvent was removed underreduced pressure and the residue was partitioned between water anddichloromethane. The layers were separated and the aqueous phase wasextracted twice with dichloromethane. The combined organic phases weredried and concentrated. Chromatography on silica gel eluting with amixture of pentane and ethyl acetate (3:1, v/v) gave5-tert-butoxycarbonylamino-nicotinic acid ethyl ester (4.79 g). Thisester was dissolved in methanol (45 mL) and treated with 1 N NaOH (54mL, 54 mmol). After stirring 2 hours, volatiles were evaporated underreduced pressure and the residue was treated with 1 N HCl until theresultant slurry reached pH 3. The precipitate was collected byfiltration, washed with water, and dried to afford5-tert-butoxycarbonylamino-nicotinic acid (4.21 g): ¹H NMR (300 MHz,DMSO-d₆) δ13.39 (br s, 1H), 9.82 (s, 1H), 8.78 (d, J=2.5 Hz, 1H), 8.69(d, J=1.9 Hz, 1H), 8.45-8.50 (m, 1H), 1.50 (s, 9H); ¹³C NMR (75 MHz,DMSO-d₆) δ166.2, 152.7, 143.4, 143.2, 136.2, 126.3, 124.9, 80.0, 27.9;MS (ESI) m/z 239 (M+H).

B.{5-[1-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidin-1-yl)methanoyl]-pyridin-3-yl}carbamicacid tert-butyl ester

To a 0° C. solution of4-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidine(0.1545 g, 0.3956 mmol, EXAMPLE 1B),5-tert-butoxycarbonylamino-nicotinic acid (0.0966 g, 0.4055 mmol),1-hydroxy-7-azabenzotriazole (0.0290 g, 0.2131 mmol), and1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.1500 g,0.7824 mmol) in dimethylformamide (5.0 mL) was added pyridine (0.065 mL,0.8037 mmol). The reaction mixture was stirred 30 minutes at 0° C., thenallowed to warm to room temperature under inert atmosphere. After 16hours at ambient temperature the reaction solution was diluted withethyl acetate (30 mL), washed with saturated ammonium chloride (2×15mL), saturated sodium bicarbonate (15 mL), and brine (15 mL). Theorganic phase was dried over magnesium sulfate, filtered, and evaporatedto dryness. The residue was purified by silica gel chromatographyeluting with a mixture of ethyl acetate and methylene chloride (1:1,v/v) to give{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidin-1-yl)methanoyl]-pyridin-3-yl}carbamicacid tert-butyl ester as a colorless oil (0.1812 g): TLC,50:50-methylene chloride:ethyl acetate, R_(f)=0.20. ¹H NMR (300 MHz,CDCl₃) δ8.67 (d, J=2.6 Hz, 1H), 8.34 (d, J=1.4 Hz, 1H), 8.09 (s, 1H),7.93 (s, 1H), 7.21-7.35 (m, 1H), 7.08-7.18 (m, 3H), 4.81-4.93 (m, 1H),4.78 (s, 2H), 3.81-3.93 (br m, 1H), 3.11-3.28 (br m, 1H), 2.70-2.96 (m,2H), 1.51 (s, 9H), 1.45 (s, 18H), 1.40-2.02 (m partially obscured, 4H);¹³C NMR (75 MHz, CDCl₃) δ167.5, 152.6, 152.5, 144.8, 141.3, 141.0,138.9, 135.7, 131.8, 128.5, 125.6, 125.3, 125.2, 124.1, 82.4, 81.0,77.2, 49.3, 42.5, 28.1, 27.8; MS (CI) m/z 611 (M+H).

C.(4-Bromo-2-fluoro-benzyl)-{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-carbamicacid dimethyl-ethyl ester

To a solution of{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidin-1-yl)methanoyl]-pyridin-3-yl}carbamicacid tert-butyl ester (0.0745 g, 0.1220 mmol) in dimethylformamide (2.0mL) was added sodium hydride (61% suspension in mineral oil, 0.0216 g,0.5499 mmol). Deprotonation was allowed to occur over 3 minutes whilestirring under inert atmosphere. 4-Bromo-2-fluorobenzyl bromide (0.1559g, 0.5819 mmol) was added to the anion solution. The mixture was stirredan additional 10 minutes, then quenched with water (5.0 mL). Thereaction solution was extracted with ethyl acetate (15 mL), and theorganic phase was washed with brine (2×10 mL), dried over magnesiumsulfate, filtered, and evaporated to dryness. Purification of theresidue on silica gel eluting first with ethyl acetate/methylenechloride/hexane (1:1:2, v/v/v) and then with ethyl acetate and methylenechloride (1:1, v/v) afforded(4-bromo-2-fluoro-benzyl)-{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl)}-carbamicacid dimethyl-ethyl ester as a colorless oil (0.0917 g): TLC,50:50-methylene chloride:ethyl acetate, R_(f)=0.59. ¹H NMR (300 MHz,CDCl₃) δ8.47-8.51 (m, 2H), 7.61 (br s, 1H), 7.07-7.32 (m, 7H), 4.89 (s,2H), 4.78 (s, 2H), 4.77-4.92 (m partially obscured, 1H), 3.68-3.83 (brm, 1H), 3.09-3.24 (br m, 1H), 2.70-2.97 (m, 2H), 1.45 (s, 18H), 1.44 (s,9H), 1.30-2.04 (m partially obscured, 4H); ¹³C NMR (75 MHz, CDCl₃)δ167.0, 160.4 (d, 250.8), 154.0, 152.7, 148.5, 144.9, 139.0, 138.7,132.2, 131.9, 130.7, 129.7, 127.9 (d, 3.4), 125.8, 125.7, 125.3, 123.8(d, 14.5), 121.8 (d, 9.7), 119.3 (d, 24.8), 82.5, 82.2, 49.5, 46.9,42.6, 32.8 (br), 28.4, 28.2, 28.0; ¹⁹F NMR (282 MHz, CDCl₃) δ− 114.9; MS(CI) m/z 797 (M+H).

D.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-[5-(4-bromo-2-fluoro-benzylamino)-pyridin-3-yl]-methanonetrihydrochloride

(4-Bromo-2-fluoro-benzyl)-{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl)-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-carbamicacid dimethyl-ethyl ester (0.0806 g, 0.1010 mmol) was treated with 4 MHCl in 1,4-dioxane (2.0 mL, 8.0 mmol) and stirred at ambienttemperature. After 25 minutes the reaction mixture was diluted withisopropyl alcohol (0.5 mL) and stirring was continued for an additional2.5 hours. Dripping the reaction solution into ether (40 mL) withvigorous stirring afforded a white precipitate which was collected byfiltration, washed with fresh ether (3.0 mL), and dried to afford1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[5-(4-bromo-2-fluoro-benzylamino)-pyridin-3-yl]-methanonetrihydrochloride (0.0563 g): ¹H NMR (300 MHz, DMSO-d₆) δ8.39 (br s, 2H),8.16 (d, J=2.7 Hz, 1H), 8.08 (s, 1H), 7.16-7.70 (m, 8H), 4.49-4.64 (brm, 1H), 4.46 (s, 2H), 4.05-4.30 (m, 1H), 4.00 (AB q, J=5.7 Hz, 2H),3.01-3.25 (m, 1H), 2.77-2.95 (m, 2H), 1.75-1.92 (m, 1H), 1.45-1.75 (brm, 3H); ¹⁹F NMR (282 MHz, DMSO-d₆) δ −114.1; MS (ESI) m/z 497 (M+H).

EXAMPLE 1061-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(5-benzylamino-pyridin-3-yl)-methanonetrihydrochloride

A.Benzyl-{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-carbamicacid dimethyl-ethyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using benzyl bromide in place of 4-bromo-2-fluorobenzylbromide, there was preparedbenzyl-{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-carbamicacid dimethyl-ethyl ester as a yellow oil. TLC, 50:50-methylenechloride:ethyl acetate, R_(f)=0.48. ¹H NMR (300 MHz, CDCl₃) δ8.52 (d,J=2.2 Hz, 1H), 8.46 (d, J=1.2 Hz, 1H), 7.56 (s, 1H), 7.04-7.38 (m, 9H),4.89 (s, 2H), 4.78 (s, 2H), 4.75-4.90 (m partially obscured, 1H),3.63-3.88 (br m, 1H), 3.00-3.19 (br m, 1H), 2.68-2.90 (m, 2H), 1.45 (s,18H), 1.44 (s, 9H), 1.37-2.04 (m, 4H); ¹³C NMR (75 MHz, CDCl₃) δ167.0,154.1, 152.6, 148.4, 144.8, 144.5, 138.9, 137.5, 132.0, 131.5, 128.6,128.5, 127.5, 127.2, 125.7, 125.5, 125.2, 82.4, 81.6, 53.4, 49.4, 42.5,33.8, 28.3, 28.1, 27.9; MS (CI) m/z 701 (M+H).

B.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(5-benzylamino-pyridin-3-yl)-methanonetrihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but usingbenzyl-{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-carbamicacid dimethyl-ethyl ester, there was prepared1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(5-benzylamino-pyridin-3-yl)-methanonetrihydrochloride as a white solid. ¹H NMR (300 MHz, DMSO-d₆) δ8.45 (brs, 2H), 8.13 (d, J=2.5 Hz, 1H), 8.08 (d, J=1.0 Hz, 1H), 7.54 (s, 1H),7.47 (s, 1H), 7.18-7.45 (m, 8H), 4.50-4.63 (br m, 1H), 4.45 (s, 2H),4.02-4.12 (m, 1H), 3.99 (AB q, J=5.5 Hz, 2H), 3.05-3.25 (m, 1H),2.70-2.95 (m, 2H), 1.75-1.90 (br m, 1H), 1.50-1.70 (br m, 3H); MS (ESI)m/z 401 (M+H).

EXAMPLE 1071-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{5-[(naphthalen-2-ylmethyl)-amino]-pyridin-3-yl}-methanonetrihydrochloride

A.{5-[1-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidin-1-yl)-methanoyl}-pyridin-3-yl}-naphthalen-2-ylmethyl-carbamicacid dimethyl-ethyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using 2-(bromomethyl)naphthalene in place of4-bromo-2-fluorobenzyl bromide, there was prepared{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidin-1-yl)-methanoyl}-pyridin-3-yl}-naphthalen-2-ylmethyl-carbamicacid dimethyl-ethyl ester as a colorless oil. TLC, 50:50-methylenechloride:ethyl acetate, R_(f)=0.42. 1H NMR (300 MHz, CDCl₃) δ8.55 (d,J=1.8 Hz, 1H), 8.13 (d, J=187.5 Hz, 1H), 7.68-7.83 (m, 3H), 7.60 (s,1H), 7.54 (br s, 1H), 7.35-7.49 (m, 3H), 7.21-7.29 (m partiallyobscured, 1H), 7.16 (d, J=7.7 Hz, 1H), 7.08 (s, 1H), 7.01 (d, J=7.7 Hz,1H), 5.00-5.08 (m, 2H), 4.77 (s, 2H), 3.48-3.62 (br m, 1H), 2.59-3.03(m, 3H), 1.45 (s, 27H), 1.27-1.95 (m, 4H); ¹³C NMR (75 MHz, CDCl₃)δ166.9, 154.3, 152.6, 148.6, 144.8, 144.7, 138.9, 138.8, 134.9, 133.3,132.8, 132.2, 131.6, 128.6, 127.7, 126.3, 126.2, 126.0, 125.8, 125.5,125.3, 125.2, 82.4, 81.8, 53.6, 49.4, 42.5, 33.2, 28.4, 28.2, 28.0; MS(CI) m/z 752 (M+H).

B.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-{5-[(naphthalen-2-ylmethyl)-amino]-pyridin-3-yl}-methanonetrihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but using{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidin-1-yl)-methanoyl}-pyridin-3-yl)-naphthalen-2-ylmethyl-carbamicacid dimethyl-ethyl ester, there was prepared1-{4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{5-[(naphthalen-2-ylmethyl)-amino]-pyridin-3-yl}-methanonetrihydrochloride as a as a white solid. ¹H NMR (300 MHz, DMSO-d₆) δ8.34(br s, 2H), 8.17 (s, 1H), 8.03 (s, 1H), 7.75-7.97 (m, 4H), 5.58-7.77 (m,1H), 7.25-7.57 (m, 6H), 7.22 (d, J=7.2 Hz, 1H), 4.61 (s, 2H), 4.50-4.68(m partially obscured, 1H), 4.10-4.35 (m, 1H), 4.00 (AB q, J=5.7 Hz,2H), 2.91-3.12 (m, 1H), 2.66-2.90 (m, 2H), 1.70-1.89 (m, 1H), 1.36-1.69(m, 3H); MS (ESI) n/z 451 (M+H).

EXAMPLE 1081-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[5-(4-bromo-benzylamino)-pyridin-3-yl]-methanonetrihydrochloride

A.(4-Bromobenzyl)-{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-carbamicacid dimethyl-ethyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using 4-bromobenzyl bromide in place of 4-bromo-2-fluorobenzylbromide, there was prepared(4-bromobenzyl)-{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-carbamicacid dimethyl-ethyl ester as a colorless oil. TLC, 50:50-methylenechloride:ethyl acetate, R_(f)=0.41. ¹H NMR (300 MHz, CDCl₃) δ8.45-8.51(m, 2H), 7.56 (br s, 1H), 7.43 (d, J=8.4 Hz, 2H), 7.24-7.30 (m partiallyobscured, 1H), 7.11 (d, J=8.4 Hz, 2H), 6.96-7.17 (m partially obscured,3H), 4.83 (s, 2H), 4.77 (s, 2H), 4.75-4.87 (m partially obscured, 1H),3.65-3.80 (br m, 1H), 3.05-3.23 (br m, 1H), 2.69-2.91 (m, 2H), 1.45 (s,18H), 1.43 (s, 9H), 1.30-2.00 (m, 4H); ¹³C NMR (75 MHz, CDCl₃) δ166.8,154.0, 152.5, 148.4, 144.7, 138.9, 138.7, 136.5, 132.1, 131.8, 131.7,131.5, 129.0, 128.6, 125.7, 125.5, 125.2, 121.4, 82.4, 81.9, 52.8, 49.3,42.5, 33.5, 28.3, 28.1, 27.9; MS (CI) m/z 781 (M+H).

B.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-[5-(4-bromo-benzylamino)-pyridin-3-yl]-methanonetrihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but using(4-bromobenzyl)-{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-carbamicacid dimethyl-ethyl ester, there was prepared1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[5-(4-bromo-benzylamino)-pyridin-3-yl]-methanonetrihydrochloride as a cream-colored solid. ¹H NMR (300 MHz, DMSO-d₆)δ8.34 (br s, 2H), 8.11 (d, J=2.5 Hz, 1H), 8.04 (s, 1H), 7.52 (d, J=8.5Hz, 2H), 7.34 (d, J=8.5 Hz, 2H), 7.15-7.67 (m, 5H), 4.49-4.64 (br m,1H), 4.42 (s, 2H), 4.05-4.15 (m, 1H), 4.01 (AB q, J=5.7 Hz, 2H),3.00-3.20 (m, 1H), 2.70-2.90 (m, 2H), 1.72-1.88 (m, 1H), 1.45-1.70 (m,3H); MS (ESI) m/z 479 (M+H).

EXAMPLE 1093-[(5-}1-[4-(3-aminomethyl-phenyl)piperidin-1-yl]-methanoyl}-pyridin-3-ylamino)-methyl]-benzonitriletrihydrochloride

A.{5-[1-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-(3-cyano-benzyl)-carbamicacid dimethyl-ethyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but α-bromo-m-tolunitrile in place of 4-bromo-2-fluorobenzylbromide, there was prepared{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-(3-cyano-benzyl)-carbamicacid dimethyl-ethyl ester as a yellow oil. TLC, 50:50-methylenechloride:ethyl acetate, R_(f)=0.44. ¹H NMR (300 MHz, CDCl₃) δ8.46-8.52(m, 2H), 7.51-7.65 (m, 3H), 7.36-7.50 (m, 2H), 7.24-7.31 (m partiallyobscured, 1H), 7.03-7.18 (m, 3H), 4.92 (s, 2H), 4.79-4.92 (m partiallyobscured, 1H), 4.78 (s, 2H), 3.70-3.85 (br m, 1H), 3.10-3.28 (br m, 1H),2.71-2.99 (m, 2H), 1.45 (s, 18H), 1.44 (s, 9H), 1.30-2.05 (m partiallyobscured, 4H); ¹³C NMR (75 MHz, CDCl₃) δ166.7, 153.8, 152.5, 148.1,145.2, 144.7, 139.2, 138.9, 138.7, 132.1, 131.9, 131.5, 131.2, 130.6,129.6, 128.6, 125.6, 125.5, 125.2, 118.3, 112.9, 82.4, 80.6, 52.8, 49.3,42.4, 33.5, 28.3, 28.0, 27.9; MS (CI) m/z 727 (M+H).

B.3-[(5-{1-[4-(3-Aminomethyl-phenyl)piperidin-1-yl]-methanoyl}-pyridin-3-ylamino)-methyl]-benzonitriletrihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but using{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-(3-cyano-benzyl)-carbamicacid dimethyl-ethyl ester, there was prepared3-[(5-{1-[4-(3-aminomethyl-phenyl)piperidin-1-yl]-methanoyl}-pyridin-3-ylamino)-methyl]-benzonitriletrihydrochloride as a white solid. ¹H NMR (300 MHz, DMSO-d₆) δ8.33 (brs, 2H), 8.13 (d, J=2.5 Hz, 1H), 8.02 (s, 1H), 7.80-7.91 (m, 1H),7.63-7.75 (m, 2H), 7.42-7.58 (m, 2H), 7.20-7.7.41 (m, 4H), 4.51 (s, 2H),4.40-4.62 (m partially obscured, 1H), 4.10-4.25 (m, 1H), 4.00 (AB q,J=5.7 Hz, 2H), 2.90-3.20 (m, 1H), 2.72-2.93 (m, 2H), 1.75-1.90 (br m,1H), 1.45-1.70 (br m, 3H); MS (ESI) m/z 426 (M+H).

EXAMPLE 1101-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[5-(2-chloro-4-fluoro-benzylamino)-pyridin-3-yl]-methanonetrihydrochloride

A.{5-[1-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-(2-chloro-4-fluoro-benzyl)-carbamicacid dimethyl-ethyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using 2-chloro-4-fluorobenzyl bromide in place of4-bromo-2-fluorobenzyl bromide, there was prepared{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl)-(2-chloro-4-fluoro-benzyl)-carbamicacid dimethyl-ethyl ester as a colorless oil. TLC, 50:50-methylenechloride:ethyl acetate, R_(f)=0.48. ¹H NMR (300 MHz, CDCl₃) δ8.51 (d,J=2.2 Hz, 1H), 8.46 (d, J=1.8 Hz, 1H), 7.62 (s, 1H), 7.24-7.34 (m, 2H),7.04-7.19 (m, 4H), 6.97 (td, J=8.2, 2.5 Hz, 1H), 4.96 (s, 2H), 4.77 (s,2H), 4.75-4.90 (m partially obscured, 1H), 3.70-3.85 (br m, 1H),3.05-3.25 (br m, 1H), 2.70-2.90 (m, J=21.45, s Hz, 18H), 1.44 (s, 9H),1.30-2.05 (m, 4H); ¹³C NMR (75 MHz, CDCl₃) δ166.9, 161.8 (d, 250.1),153.8, 152.6, 148.1, 144.7, 144.6, 138.9, 138.6, 133.6 (d, 9.7), 131.8,131.7, 130.8 (d, 3.4), 129.8 (d, 7.6), 128.6, 125.7, 125.6, 125.2, 117.0(d, 24.9), 114.3 (d, 21.4), 82.4, 82.1, 50.3, 49.4, 42.5, 33.8, 28.3,28.1, 27.9; ¹⁹F NMR (282 MHz, CDCl₃) δ −112.0; MS (CI) m/z 754 (M+H).

B.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-[5-(2-chloro-4-fluoro-benzylamino)-pyridin-3-yl]-methanonetrihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but using{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)aminomethyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-(2-chloro-4-fluoro-benzyl)-carbamicacid dimethyl-ethyl ester, there was prepared1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl-1-[5-(2-chloro-4-fluoro-benzylamino)-pyridin-3-yl]-methanonetrihydrochloride as a white solid. ¹H NMR (300 MHz, DMSO-d₆) δ8.34 (brs, 2H), 8.15 (d, J=2.5 Hz, 1H), 8.07 (s, 1H), 7.12-7.55 (m, 8H),4.50-4.65 (br m, 1H), 4.46 (s, 2H), 4.12-4.24 (br m, 1H), 4.00 (AB q,J=5.8 Hz, 2H), 3.05-3.20 (br m, 1H), 2.70-2.90 (m, 2H), 1.72-1.90 (br m,1H), 1.48-1.73 (br m, 3H); ¹⁹F NMR (282 MHz, DMSO-d₆) δ −112.6; MS (ESI)m/z 453 (M+H).

EXAMPLE 1111-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-[5-(4-trifluoromethoxy-benzylamino)-pyridin-3-yl]-methanonetrihydrochloride

A.[5-[1-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl)-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-(4-trifluoromethoxy-benzyl)-carbamicacid dimethyl-ethyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using 4-(trifluoromethoxy)benzyl bromide in place of4-bromo-2-fluorobenzyl bromide, there was prepared{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-(4-trifluoromethoxy-benzyl)-carbamicacid dimethyl-ethyl ester as a colorless oil. TLC, 50:50-methylenechloride:ethyl acetate, R_(f)=0.48. ¹H NMR (300 MHz, CDCl₃) δ8.45-8.53(m, 2H), 7.60 (s, 1H), 7.20-7.30 (m, 3H), 7.05-7.20 (m, 5H), 4.88 (s,2H), 4.77 (s, 2H), 4.75-4.90 (m partially obscured, 1H), 3.70-3.84 (brm, 1H), 3.08-3.24 (br m, 1H), 2.70-2.93 (m, 2H), 1.45 (s, 18H), 1.44 (s,9H), 1.35-2.05 (m, 4H); ¹³C NMR (75 MHz, CDCl₃) δ166.9, 154.0, 152.6,148.3, 144.7, 144.6, 138.9, 138.8, 136.3, 132.2, 131.9, 128.7, 128.6,125.7, 125.6, 125.2, 121.2, 120.1 (q, 262), 82.4, 82.0, 52.7, 49.4,42.5, 32.3, 28.3, 28.1, 27.9; ¹⁹F NMR (282 MHz, CDCl₃) δ −57.4; MS (CI)m/z 786 (M+H).

B.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-[5-(4-trifluoromethoxy-benzylamino)-pyridin-3-yl]-methanonetrihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but using{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl)-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-(4-trifluoromethoxy-benzyl)-carbamicacid dimethyl-ethyl ester, there was prepared1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[5-(4-trifluoromethoxy-benzylamino)-pyridin-3-yl]-methanonetrihydrochloride as a white solid. ¹H NMR (300 MHz, DMSO-d₆) δ8.35 (brs, 2H), 8.12 (d, J=2.8 Hz, 1H), 8.05 (s, 1H), 7.20-7.75 (m, 9H),4.50-4.65 (m, 1H), 4.48 (s, 2H), 4.05-4.20 (m, 1H), 4.00 (AB q, J=5.9Hz, 2H), 3.05-3.25 (m, 1H), 2.70-2.90 (m, 2H), 1.75-1.90 (m, 1H),1.50-1.70 (br m, 3H); ¹⁹F NMR (282 MHz, DMSO-d₆) δ −56.3; MS (ESI) m/z485 (M+H).

EXAMPLE 1121-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{5-[(pyridin-3-ylmethyl)-amino]-pyridin-3-yl}-methanonetetrahydrochloride

A.{5-[1-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-pyridin-3-ylmethyl-carbamicacid dimethyl-ethyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using 3-(chloromethyl)pyridine hydrochloride in place of4-bromo-2-fluorobenzyl bromide, there was prepared{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-pyridin-3-ylmethyl-carbamicacid dimethyl-ethyl ester as a colorless oil. TLC, 15:85-isopropylalcohol:methylene chloride, R_(f)=0.54. ¹H NMR (300 MHz, CDCl₃)δ8.46-8.56 (m, 4H), 7.53-7.62 (m, 2H), 7.22-7.31 (m partially obscured,2H), 7.05-7.18 (m, 3H), 4.90 (s, 2H), 4.77 (s, 2H), 4.75-4.99 (mpartially obscured, 1H), 3.69-3.83 (br m, 1H), 3.05-3.25 (br m, 1H),2.70-2.96 (m, 2H), 1.45 (s, 18H), 1.44 (s, 9H), 1.20-2.03 (m, 4H); ¹³CNMR (75 MHz, CDCl₃) δ166.8, 154.0, 152.6, 149.1, 149.0, 148.6, 144.9,144.7, 138.9, 138.7, 135.1, 133.1, 132.4, 131.9, 128.7, 125.7, 125.6,125.3, 123.6, 82.5, 82.2, 51.2, 49.4, 42.6, 33.9, 28.4, 28.2, 28.0; MS(CI) m/z 702 (M+H).

B.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-[5-[(pyridin-3-ylmethyl)-amino]-pyridin-3-yl}-methanonetetrahydrochloride

{5-[1-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-pyridin-3-ylmethyl-carbamicacid dimethyl-ethyl ester (0.0250 g, 0.0356 mmol) was treated with 5-6 MHCl in isopropanol (1.0 mL, 8.0 mmol) and stirred at ambienttemperature. After 90 minutes the reaction mixture was diluted withmethyl alcohol (0.5 mL) and stirring was continued for an additional 75minutes. Dripping the reaction solution into ether (40 mL) with vigorousstirring afforded a white precipitate which was collected by filtration,washed with fresh ether (3.0 mL), and dried to afford1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{5-[(pyridin-3-ylmethyl)-amino]-pyridin-3-yl}-methanonetetrahydrochloride (0.0160 g): ¹H NMR (300 MHz, DMSO-d₆) δ8.60-8.95 (m,2H), 8.39 (br s, 2H), 8.29 (d, J=8.0 Hz, 1H), 7.97-8.25 (m, 2H),7.65-7.85 (m, 2H), 7.47 (d, J=8.0 Hz, 2H), 7.20-7.38 (m, 3H), 4.63 (s,2H), 4.43-4.61 (m partially obscured, 1H), 4.00 (AB q, J=5.8 Hz, 2H),3.05-3.25 (m partially obscured, 1H), 2.72-2.95 (m, 2H), 1.80-1.88 (m,1H), 1.47-1.77 (m, 3H); MS (CI) m/z 402 (M+H).

EXAMPLE 1131-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{5-[(pyridin-2-ylmethyl)-amino]-pyridin-3-yl}-methanonetetrahydrochloride

A.{5-[1-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-pyridin-2-ylmethyl-carbamicacid dimethyl-ethyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using 2-(chloromethyl)pyridine hydrochloride in place of4-bromo-2-fluorobenzyl bromide, there was prepared{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidin-1-yl}-methanoyl]-pyridin-3-yl}-pyridin-2-ylmethyl-carbamicacid dimethyl-ethyl ester as a colorless oil. TLC, 50:50-methylenechloride:ethyl acetate, R_(f)=0.09. ¹H NMR (300 MHz, CDCl₃) δ8.67 (d,J=2.3 Hz, 1H), 8.52 (d, J=4.7 Hz, 1H), 8.44 (d, J=1.8 Hz, 1H), 7.81 (s,1H), 7.59-7.72 (m, 1H), 7.22-7.31 (m partially obscured, 2H), 7.00-7.20(m, 4H), 4.97 (s, 2H), 4.77 (s, 2H), 4.72-4.90 (m partially obscured,1H), 3.74-3.89 (br m, 1H), 3.04-3.25 (br m, 1H), 2.69-2.94 (m, 2H), 1.45(s, 18H), 1.41 (s, 9H), 1.23-2.03 (m partially obscured, 4H); MS (CI)m/z 702 (M+H).

B.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-{5-[(pyridin-2-ylmethyl)-amino]-pyridin-3-yl}-methanonetetrahydrochloride

By proceeding in a similar manner to the method described in EXAMPLE112B, but using{5-[1-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-pyridin-2-ylmethyl-carbamicacid dimethyl-ethyl ester, there was prepared1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{5-[pyridin-2-ylmethyl)-amino]-pyridin-3-yl}-methanonetetrahydrochloride as a white solid. MS (ESI) m/z 402 (M+H).

In a similar manner to the methods described in EXAMPLES 105 and 112,the following compounds are prepared:

EXAMPLE 1141-4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{5-[(pyridin-4-ylmethyl)-amino]-pyridin-3-yl)}-methanonetetrahydrochloride EXAMPLE 1151-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(3-benzylamino-phenyl)-methanonedihydrochloride

A.[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester

By proceeding in a similar manner to the method described in EXAMPLE105B, but using 3-(Boc-amino)benzoic acid in place of5-tert-butoxycarbonylamino-nicotinic acid, there was prepared[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester as a white solid. ¹H NMR (300 MHz, CDCl₃)δ7.40-7.50 (m, 2H), 7.22-7.37 (m, 2H), 7.04-7.15 (m, 4H), 4.77-4.90 (brm, 1H), 4.76 (s, 2H), 3.81-3.96 (br m, 1H), 3.05-3.20 (br m, 1H),2.68-2.90 (m, 2H), 1.52 (s, 9H), 1.45 (s, 18H), 1.35-1.85 (m partiallyobscured, 4H) ); MS (CI) m/z 610 (M+H).

B.Benzyl-[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using benzyl bromide in place of 4-bromo-2-fluorobenzylbromide and using[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester, there was preparedbenzyl-[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester as a white solid. ¹H NMR (300 MHz, CDCl₃)δ7.03-7.34 (m, 13H), 4.84 (br s, 2H), 4.78-4.90 (m partially obscured,1H), 4.77 (s, 2H), 3.69-3.85 (br m, 1H), 2.90-3.10 (br m, 1H), 2.65-2.88(m, 2H), 1.45 (s, 18H), 1.41 (s, 9H), 1.35-1.95 (m partially obscured,4H) ); MS (CI) m/z 700 (M+H).

C.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(3-benzylamino-phenyl)-methanonedihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but using preparedbenzyl-[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester, there was prepared1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(3-benzylamino-phenyl)-methanonedihydrochloride as a white solid. MS (ESI) m/z 400 (M+H).

EXAMPLE 1161-{4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[(naphthalen-2-ylmethyl)-amino]-phenyl}-methanonedihydrochloride

A.[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-naphthalen-2-ylmethyl-carbamicacid tert-butyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using 2-(bromomethyl)naphthalene in place of4-bromo-2-fluorobenzyl bromide and using[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester, there was prepared[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-naphthalen-2-ylmethyl-carbamicacid tert-butyl ester as a white solid. MS (ESI) m/z 650 (M+H).

B.1-{4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[(naphthalen-2-ylmethyl)-amino]-phenyl}-methanonedihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but using[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-naphthalen-2-ylmethyl-carbamicacid tert-butyl ester, there was prepared1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[(naphthalen-2-ylmethyl)-amino]-phenyl}-methanonedihydrochloride as a white solid. MS (ESI) m/z 450 (M+H).

EXAMPLE 1173-[(3-{1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-phenylamino)-methyl]-benzonitriledihydrochloride

A.[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-(3-cyano-benzyl)-carbamicacid tert-butyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using α-bromo-m-tolunitrile in place of 4-bromo-2-fluorobenzylbromide and using[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester, there was prepared[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-(3-cyano-benzyl)-carbamicacid tert-butyl ester as a white solid. MS (CI) m/z 725 (M+H).

B.3-[(3-{1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-phenylamino)-methyl]-benzonitriledihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-(3-cyano-benzyl)-carbamicacid tert-butyl ester, there was prepared3-[(3-{1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-phenylamino)-methyl]-benzonitriledihydrochloride as a white solid. MS (ESI) m/z 425 (M+H).

EXAMPLE 1181-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(4-bromo-benzylamino)-phenyl]-methanonedihydrochloride

A.(4-Bromo-benzyl)-[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using 4-bromobenzyl bromide in place of 4-bromo-2-fluorobenzylbromide and using[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester, there was prepared(4-bromo-benzyl)-[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester as a clear oil. MS (CI) m/z 778 (M+H).

B.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(4-bromo-benzylamino)-phenyl]-methanonedihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but using(4-bromo-benzyl)-[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester, there was prepared1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(4-bromo-benzylamino)-phenyl]-methanonedihydrochloride as a white solid. MS (ESI) m/z 480 (M+H).

EXAMPLE 1191-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[(pyridin-2-ylmethyl)-amino]-phenyl}-methanonetrihydrochloride

A.[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-pyridin-2-ylmethyl-carbamicacid tert-butyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using 2-picolyl chloride hydrochloride in place of4-bromo-2-fluorobenzyl bromide and using[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester, there was prepared[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-pyridin-2-ylmethyl-carbamicacid tert-butyl ester as a white solid. ¹H NMR (300 MHz, CDCl₃): δ8.53(d, 1H), 7.60-7.70 (m, 2H), 7.29-7.37 (m, 4H), 7.08-7.24 (m, 5H), 4.97(s, 2H), 4.70-4.90 (m partially obscured, 1H), 4.77 (s, 2H), 3.75-3.95(br m, 1H), 2.65-3.20 (br m, 3H), 1.40-2.00 (m partially obscured, 4H),1.45 (s, 18H), 1.39 (s, 9H). MS (ESI): m/z 701 (M+H).

B.1-{4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[(pyridin-2-ylmethyl)-amino]-phenyl}-methanonetrihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but using[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-pyridin-2-ylmethyl-carbamicacid tert-butyl ester, there was prepared1-{4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[(pyridin-2-ylmethyl)-amino]-phenyl}-methanonetrihydrochloride as a light yellow solid. ¹H NMR [300 MHz, (CD₃)₂SO]:δ8.69 (d, 1H), 8.34 (br s, 3H), 8.19 (tr, 1H), 7.73 (d, 1H), 7.63 (tr,1H), 7.25-7.42 (m, 4H), 7.14 (tr, 1H), 6.68 (d, 1H), 6.61 (m, 2H),4.40-4.70 (br m partially obscured, 1H), 4.61 (s, 2H), 4.01 (q, 2H),3.70-3.95 (br m partially obscured, 1H), 2.90-3.15 (br m, 1H), 2.65-2.90(br m, 2H), 1.35-1.95 (br m, 4H). MS (ESI): m/z 401 (M+H).

EXAMPLE 1201-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[(pyridin-3-ylmethyl)-amino]-phenyl}-methanonetrihydrochloride

A.[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-pyridin-3-ylmethyl-carbamicacid tert-butyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using 3-picolyl chloride hydrochloride in place of4-bromo-2-fluorobenzyl bromide and using[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester, there was prepared[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-pyridin-3-ylmethyl-carbamicacid tert-butyl ester as a cream oil. ¹H NMR (300 MHz, CDCl₃): δ8.49 (brs, 2H), 7.57 (d, 1H), 7.33 (m, 1H), 7.07-7.24 (m, 8H), 4.70-4.95 (mpartially obscured, 1H), 4.85 (s, 2H), 4.77 (s, 2H), 3.65-3.90 (br m,1H), 2.65-3.15 (br m, 3H), 1.40-2.00 (m partially obscured, 4H), 1.45(s, 18H), 1.41 (s, 9H). MS (ESI): m/z 701 (M+H).

B.1-{4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[(pyridin-3-ylmethyl)-amino]-phenyl}-methanonetrihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but using[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-pyridin-3-ylmethyl-carbamicacid tert-butyl ester, there was prepared1-{4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[(pyridin-3-ylmethyl)-amino]-phenyl}-methanonetrihydrochloride as a light yellow solid. ¹H NMR [300 MHz, (CD₃)₂SO]:δ8.81 (s, 1H), 8.70 (d, 1H), 8.34 (m, 4H), 7.86 (tr, 1H), 7.25-7.41 (m,4H), 7.14 (tr, 1H), 6.67 (d, 1H), 6.59 (m, 2H), 4.40-4.70 (br mpartially obscured, 1H), 4.50 (s, 2H), 4.01 (q, 2H), 3.70-3.90 (br mpartially obscured, 1H), 2.90-3.15 (br m, 1H), 2.65-2.90 (br m, 2H),1.35-1.95 (br m, 4H). MS (ESI): m/z 401 (M+H).

EXAMPLE 1211-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[pyridin-4-ylmethyl)-amino]-phenyl}-methanonetrihydrochloride

A.[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-pyridin-4-ylmethyl-carbamicacid tert-butyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using 4-picolyl chloride hydrochloride in place of4-bromo-2-fluorobenzyl bromide and using[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester, there was prepared[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-pyridin-4-ylmethyl-carbamicacid tert-butyl ester as a cream oil. ¹H NMR (300 MHz, CDCl₃): δ8.55 (brd, 2H), 7.33 (q, 2H), 7.06-7.26 (m, 8H), 4.70-4.90 (m partiallyobscured, 1H), 4.84 (s, 2H), 4.77 (s, 2H), 3.70-3.90 (br, 1H), 268-3.15(br m, 3H), 1.40-2.00 (m partially obscured, 4H), 1.45 (s, 18H), 1.41(s, 9H). MS (ESI): m/z 701 (M+H).

B.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[(pyridin-4-ylmethyl)-amino]-phenyl}-methanonetrihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but using[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-pyridin-4-ylmethyl-carbamicacid tert-butyl ester, there was prepared1-{4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[(pyridin-4-ylmethyl)-amino]-phenyl}-methanonetrihydrochloride as a cream solid. ¹H NMR [300 MHz, (CD₃)₂SO]: δ8.76 (brs, 2H), 8.33 (br s, 3H), 7.87 (d, 2H), 7.24-7.41 (m, 4H), 7.13 (tr, 1H),6.65-7.00 (br, 1H), 6.56-6.64 (m, 3H), 4.40-4.70 (br m partiallyobscured, 1H), 4.61 (s, 2H), 4.01 (q, 2H), 3.70-3.90 (br m partiallyobscured, 1H), 2.90-3.15 (br m, 1H), 2.65-2.90 (br m, 2H), 1.35-1.95 (brm, 4H). MS (ESI): m/z 401 (M+H).

EXAMPLE 1223-[1-(5-phenylethynyl-furan-2-carbonyl)-piperidin-4-yl]-benzylaminetrifluoroacetate

A. 4-oxo-piperidine-1-carboxylic acid (trimethylsilyl) ethyl ester

A solution of 4-piperidone monohydrate. Hydrochloride (13.55 g, 88 mmol)2-trimethylsilylethyl-p-nitrophenylcarbonate (25.00 g, 88 mmol) inacetonitrile (300 ml) was treated with triethylamine (50 ml, 359 mmol)and dimethyl-aminopyridine (10.78 g, 88 mmol) and heated to reflux for 2hours. The solution was cooled and concentrated to an oil. The residuewas dissolved in dichloromethane (300 ml) and washed twice with 1Mhydrochloric acid and twice with 1M sodium hydroxide until all of theyellow color was removed from the organics. The organics were thenwashed with brine, dried over magnesium sulfate and concentrated undervacuum to give 4-oxo-piperidine-1-carboxylic acid (trimethylsilyl) ethylester as colorless oil. (19.35 g) ¹H NMR (CDCl₃, 300 MHz): δ4.24 (2H,t), 3.78 (4H, t), 2.45 (4H, t), 1.05 (2H, t), 0.05 (9H, s) MS (EI)284(M+CH₃CN)

B. 4-(3-Cyano-phenyl)-3.6-dihydro-2H-pyridine-1-carboxylic acid2-trimethylsilanyl-ethyl ester

A solution of lithium hexamethyldisilazide (60 mmol) in anhydroustetrahydrofuran (150 ml), at −78° C., was treated dropwise with asolution of 4-oxo-piperidine-1-carboxylic acid (trimethylsilyl) ethylester (13.30 g, 55 mmol) in anhydrous tetrahydrofuran (50 ml). Theaddition was over 20 minutes maintaining the internal temperature at −65to −70° C. This solution was stirred at −78° C. for 45 minutes and thentreated with a solution of N-phenyltrifluoromethanesulfonimide (19.65 g,55 mmol) in anhydrous tetrahydrofuran (75 ml). The solution was warmedto 0° C., then stirred at 0° C. for 3 hours and then concentrated undervacuum. The residue was dissolved in dichloromethane and washed withwater, dried over magnesium sulfate and concentrated to give2-(trimethylsilyl) ethyl1,2,3,6-tetrahydro-4-(trifluoromethylsulphonyloxy)-pyridine-1-carboxylateas a yellow oil (22.1 g). The material is used crude, as columnchromatography on silica gel or alumina caused the material todeteriorate. A portion of this material (20.65 g, 55 mmol) was dissolvedin acetonitrile (300 ml) and the solution was treated with3-cyanoboronic acid (8.90 g, 60 mmol), 2M sodium carbonate (82.5 ml, 165mmol) and lithium chloride (6.98 g, 165 mmol). The non-homogenousmixture was stirred vigorously and flushed with nitrogen for 5 minutes,then tetrakistriphenylphospine palladium (0) (3.10 g, 3 mmol). Themixture was heated to reflux (90° C. oil bath) for 90 minutes, thencooled and filtered. The red filtrate was concentrated and the residuewas partitioned between dichloromethane (3 lots 100 ml) and 2M sodiumcarbonate (200 ml). The combined organic extracts were dried overmagnesium sulfate and then concentrated under vacuum. The resultant oilwas subjected to chromatography silica gel eluting with a mixture ofethyl acetate, heptane and dichloromethane (1:5:1, v/v) to yield4-(3-cyano-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid2-trimethylsilanyl-ethyl ester as a yellow oil (10.46 g). ¹H NMR (CDCl₃,300 MHz): δ7.40-7.65 (m, 4H), 6.10 (m, 1H), 4.23 (t, 2H), 4.15 (d, 2H),3.70 (t, 2H), 2.45 (m, 2H), 1.12 (t, 2H), 0.05 (s, 9H).

C. 4-(3-Aminomethyl-phenyl)-piperidine-1-carboxylic acid2-trimethylsilanyl-ethyl ester hydrochloride

4-(3-Cyanophenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid2-trimethylsilanyl-ethyl ester (10.40 g, 32 mmol) was dissolved inethanol (250 ml), concentrated hydrochloric acid (3 ml, 35 mmol) and 10%palladium on carbon (50% wet, 5.0 g) was added. The mixture washydrogenated at 50 psi for 4 hours then filtered through celite andconcentrated. The oily solid obtained was triturated with ether/pentaneand 4-(3-aminomethyl-phenyl)-piperidine-1-carboxylic acid2-trimethylsilanyl-ethyl ester hydrochloride was obtained as a whitesolid (7.10 g). ¹H NMR [(CD₃)₂SO, 300 MHz]: δ8.38 (br s, 2H), 7.20-7.40(m, 4H), 4.10 (t, 4H), 3.98 (s, 2H), 2.63-3.00 (m, 3H), 1.75 (m, 2H),1.50 (m, 2H), 0.94 (t, 2H), 0.02 (s, 9H). LC-MS (ES) 335 (M⁺+H), 93%TIC.

D. (3-Piperidin-4-yl-benzyl) carbamate Wang resin

p-Nitrophenyl carbonate Wang resin (11.00 g, 15 mmol) and anhydrousdimethylformamide (100 ml) were placed in a peptide synthesis vessel andthe resin was allowed to swell for 15 minutes. This was then treatedwith 4-(3-aminomethyl-phenyl)-piperidine-1-carboxylic acid2-trimethylsilanyl-ethyl ester hydrochloride (7.50 g, 21 mmol) in 50 mldimethylformamide, dimethylaminopyridine (0.72, 6 mmol) anddiisopropylethyl-amine. The peptide vessel was shaken at roomtemperature for 24 hours, then washed thoroughly with dimethylformamide(×5), methanol (×2), dimethylformamide (×2), methanol (×2),dichloromethane (×3), methanol (×2), dichloromethane (×2), methanol(×3), and dried. The resin was then treated with tetrahydrofuran toswell the resin and then allowed to drain. Then anhydroustetrahydrofuran (100 ml) and tetrabutylammonium fluoride (75 ml, 1M intetrahydrofuran) were added and the resin shaken for 18 hours. The resinwas drained and washed with tetrahydrofuran (×5), methanol (×3),dichloromethane (×3), methanol (×3), dichloromethane (×3), methanol (×3)and dried to give (3-piperidin-4-yl-benzyl) carbamate Wang resin (12.30g).

E. 3-[1-(5-Phenylethynyl-furan-2-carbonyl)-piperidin-4-yl]-benzylaminetrifluoroacetate (3-Piperidin-4-yl-benzyl) carbamate Wang resin (60 mg,0.075 mmol) suspended in dimethylformamide (3 ml) and5-phenylethynyl-furan 2 carboxylic acid (80 mg, 0.38mmol),diisopropylcarbodiimide (48 mg, 0.38 mmol) and 1-hydroxybenzotriazole(50 mg, 0.38 mmol) were added. The mixture was shaken at roomtemperature overnight and washed with dimethylformamide (×5), methanol(×5), dichloromethane then methanol (repeat 5 times). The resin wastreated with trifluoroacetic acid and dichloromethane (1:1 v/v, 4 ml)for 45 minutes and filtered. The filtrate was concentrated to give3-[1-(5-phenylethynyl-furan-2-carbonyl)-piperidin-4-yl]-benzylaminetrifluoroacetate as a pale yellow oil (30 mg). LC-MS (ES) 385 (M⁺+H)100% TIC.

In a similar manner to the methods described in EXAMPLE 112, thefollowing compounds set forth in Table 5 were prepared as thetrifluoroacetate salts: TABLE 5 EG Structure M/Z MS area % 123

365.2 93 124

381.4 100 125

430.2 100 126

413.1 100 127

418.2 100 128

299.3 100 129

408.3 94 130

349.1 100 131

311.1 90 132

313.1 100 133

385.2 100 134

395.1 100 135

285.1 100 136

363 100 137

330.1 100 138

301.1 100 139

315.1 100 140

315.1 100 141

301.1 100 142

285.1 79 143

335.1 100 144

348.2 100 145

379.2 100 146

303.1 100 147

365.2 100 148

422.2 100 149

379.2 99 150

337.2 99 151

353.3 100 152

418.2 99 153

353.2 99 154

336.3 89 155

378.2 61 156

345.2 100 157

440.3 100 158

459 100 159

305.2 100 160

379.2 80 161

364.2 100 162

476.2 100 163

346.2 100 164

330.2 100 165

368.2 100 166

331.2 100 167

364.2 100 168

387.2 100 169

391 94 170

366.1 95 171

498.9 100 172

351.2 66 173

321.2 100 174

335.2 100 175

349.1 100 176

354.2 100 177

313.1 100 178

321.2 84 179

429.1 81 180

378.1 100 181

351.2 100 182

381.2 85 183

313.2 100 184

374.1 100 185

331.2 100 186

342 84 187

420.1 100 188

358.1 100 189

309.1 100 190

355.2 100 191

284.2 100 192

324.2 81 193

336.2 19 194

313.1 95 195

220.1 89 196

299.2 100 197

369.2 100 198

315.2 100 199

355.1 92 200

331.2 100 201

327.2 100 202

463.1 100 203

440.1 94 204

355.2 100 205

351.2 100 206

363.1 100 207

337.2 100 208

339.2 54 209

361.2 65 220

340.2 97 211

313.2 100 212

369.2 100 213

413.1 100 214

381.2 62 215

359.2 94 216

371.1 100 217

429.1 100 218

433.1 100 219

315.2 100 220

400.2 100 221

337.2 100 222

375.1 100 223

445 100 224

289.1 100 225

339.2 100 226

259.2 100 227

315.2 100 228

349.2 86 229

339.3 100 230

353.3 100 231

329.3 100 232

381.2 93 233

389.2 94 234

335.2 100 235

362.2 71 236

367.2 100 237

317.2 100 238

407.3 100 239

331.2 100 240

343.3 100 241

313.2 100 242

391.3 100 243

399.2 100 244

407.2 100 245

321.2 100 246

422.3 88 247

327.2 100 248

397.3 91 249

425.2 80 250

363.1 100 251

337.2 90 252

408.2 60 253

327.2 96 254

323.2 100 255

385.2 100 256

389.2 100 257

261.2 100 258

354.2 100 259

415.2 100 260

431.2 100 261

381.2 91 262

417.2 100 263

387.2 100 264

290.2 100 265

357.2 100 266

355.2 91 267

344.2 83 268

442.2 100 269

339.2 100 270

377.3 78 271

428.2 44 272

367.3 100 273

383.3 100 274

370.2 100 275

383.3 100 276

343.2 95 277

325.2 100 278

373.1 100 279

335.2 100 280

341.2 100 281

375.2 100

By proceeding in a similar manner to the method described in EXAMPLE 36,but using the appropriate carboxylic acid derived TFP resin in place ofthe 3,4-dichlorobenzoic acid TFP resin, the following compounds setforth in Table 6 were prepared as the trifluoroacetate salts: TABLE 6 EGStructure M/Z MS area % 282

273.3 >95% 283

369.2 >95% 284

377.4 >95% 285

379.3 >95% 286

349.3 >95% 287

422.3, 424.3 >95% 288

351.3 >95% 289

302.2 >95% 290

399.3 >95% 291

429.3 >95% 292

399.3 >95% 293

355.2 >95% 294

320.3 >95% 295

383.3 >95% 296

387.3 >95% 297

367.3   85% 298

386.3 >95% 299

385.2 >95% 300

335.3 >95% 301

275.2 >95% 302

289.3 >95% 303

289.3 >95% 304

399.3   90% 305

457.3   60% 306

337.3 >95% 307

262.2 >95% 308

381.3 >95% 309

339.2   75% 310

298.3 >95% 311

322.3 >95% 312

359.3, 360.3   75% 313

357.4 >95% 314

393.3 >95% 315

347.3 >95% 316

387.3, 389.3 >95% 317

346.3 >95% 318

375.3 >95% 319

360.3   90% 320

351.3 >95% 321

376.2 >95% 322

381.3   90% 323

365.2   65% 324

364.3 >95% 325

443.2, 445.2   75% 326

271.2 >95% 327

233.2 >95% 328

365.3 >95% 329

357.3 >95% 330

399.3   70% 331

375.3 >95% 332

379.3   80% 333

398.2, 400.2 >95% 334

365.3 >95% 335

403.3 >95% 336

385.2 387.2 >95% 337

437.3. 439.3 >95% 338

401.3 >95% 339

352.3 >95% 340

351.3 >95% 341

349.3 >95% 342

341.3 >95% 343

357.2 >95%

EXAMPLE 344[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-[1,1′;4′,1″]terphenyl-3-yl-methanonehydrochloride

A.{4-[3-N,N-Di-(tert-butoxycarbonyl)aminomethyl)-phenyl]-piperidin-1-yl}-(3-bromo-phenyl)-methanone

By proceeding in a similar manner to the method described in EXAMPLE105B, but using 3-bromobenzoic acid in place of5-tert-butoxycarbonylamino-nicotinic acid, there was prepared{4-[3-N,N-di-(tert-butoxycarbonyl)aminomethyl)-phenyl]-piperidin-1-yl}-(3-bromo-phenyl)-methanoneas a colorless oil. MS (CI) m/z 573 (M+H).

B.{4-[3-N,N-Di-(tert-butoxycarbonyl)aminomethyl)-phenyl]-piperidin-1-yl}-[1,1′;4′,1″]terphenyl-3-yl-methanone

By proceeding in a similar manner to the method described in EXAMPLE17D, but using 4-biphenylboronic acid in place of1-(5-phenylethyl-pyridine-3-carbonyl)-4-(pinacolatoboronyl)-1,2,3,6-tetrahydro-pyridineand{4-[3-N,N-di-(tert-butoxycarbonyl)aminomethyl)-phenyl]-piperidin-1-yl}-(3-bromo-phenyl)-methanonein place of N-(tert-butoxycarbonyl)-3-bromo-4-fluoro-benzylamine, therewas prepared{4-[3-N,N-di-(tert-butoxycarbonyl)aminomethyl)-phenyl]-piperidin-1-yl}-[1,1′;4′,1″]terphenyl-3-yl-methanoneas a yellow oil. MS (CI) m/z 647 (M+H).

C.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-[1,1′;4′,1″]terphenyl-3-yl-methanonehydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but using{4-[3-N,N-di-(tert-butoxycarbonyl)aminomethyl)-phenyl]-piperidin-1-yl}-[1,1′;4′,1″]terphenyl-3-yl-methanone,there was prepared[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-[1,1′;4′,1″]terphenyl-3-yl-methanonehydrochloride as a cream-colored solid. MS (CI) m/z 447 (M+H).

EXAMPLE 3453-[1-(6-chloroquinoline-3-carbonyl)-piperidin-4-yl]-benzylaminedi-hydrochloride

A. Ethyl 6-chloroquinoline-3-carboxylate

Ethyl 4,6-Dichloroquinoline-3-carboxylate [prepared as described in C.C. Price and R. M. Roberts J. Amer. Chem. Soc. 68, 1204 (1964); C. J.Ohnmacht, Jr. J. Med. Chem. 14, 17 (1971)] (2.0 g, 7.4 mmol) was addedportionwise to a solution of sodium borohydride (1.2 g, 31 mmol) in 15ml of methoxyethanol at about 0° C. The reaction mixture was warmed toroom temperature over 3 hours then diluted with ethyl acetate. Afterstandard aqueous workup (dil HCl; saturated NaHCO₃) the organic layerwas dried (NaSO₄) and concentrated to a residue. The residue was exposedto air oxidation (about 14 days) and extracted repeatedly with boilingheptane. The heptane was removed in vacuo to yield ethyl6-chloroquinoline-3-carboxylate as a beige solid. ¹H NMR [(CDCl₃), 300MHz]: δ9.38 (bs, 1H), 8.68 (s, 1H), 8.05 (d, 1H), 7.83 (s, 2H), 7.69 (d,1H), 4.40 (q, 2H), 1.39 (t, 3 H). MS(EI): 236(M⁺+H).

B. 6-Chloroquinoline-3-carboxylic acid

Ethyl 6-chloroquinoline-3-carboxylate (0.19 g, 0.81 mmol) was saponifiedby treatment with dioxane (10 ml) and 10% aqueous sodium hydroxide (10ml) at reflux for 3 hours. The dioxane was removed under vacuo; theaqueous solution remaining was acidified with HCl. The precipitatedproduct was collected and washed with water to isolate6-chloroquinoline-3-carboxylic acid as an off-white solid (0.14 g, 0.67mmol). ¹H NMR [(CD₃OD), 300 MHz]: δ9.35 (s, 1H), 8.95 (s, 1H), 8.17 (s,1H), 8.1 (d, 2H), 7.87 (d, 1H).

C.N,N-bis-(tert-butoxycarbonyl)-3-[1-(6-chloroquinoline-3-carbonyl)-piperidin-4-yl]benzylamine

By proceeding in a similar manner to the method described in EXAMPLE 1C,but using 6-chloroquinoline-3-carboxylic acid in place of5-phenylethynyl-pyridine-3-carboxylic acid, crude title compound wasprepared. The crude product was purified by flash chromatography (25-50%ethyl acetate/Heptane) to yield the title compound as a white amorphoussolid. ¹H NMR[(CDCl₃), 300 MHz]: δ8.98 (bs, 1H), 8.20 (s, 1H), 8.05 (d,1H), 7.88 (s, 1H), 7.72 (d, 1H), 7.08-7.31 (m, 4H), 4.93 (br m, 1H),4.78 (s, 2H), 3.90 (br m, 1H), 3.27 (br m, 1H), 3.95 (br m, 1H), 2.82(m, 1H), 1.6-2.1 (br m, 4H), 1.47 (s, 18H).

D. 3-[-(6-Chloroquinoline-3-carbonyl)-piperidin-4-yl]-benzylamine

N,N-bis-(tert-butoxycarbonyl)-3-[1-(6-Chloroquinoline-3-carbonyl)-piperidin-4-yl]benzylamine(0.055 g, 0.095 mmol) was treated with a solution of 15% trifluoroaceticacid in methylene chloride (5 ml) at 0° C. The reaction was warmed toambient temperature over 2.5 hr and the solvents were removed in vacuo.The residue was triturated with ether to yield the title compound (0.033g, 0.087 mmol) as an amorphous solid. ¹H NMR[(CD₃)₂SO, 500 MHz]: δ8.95(s, 1H), 8.44 (s, 1H), 8.20 (s, 1H), 8.07 (d, 1H), 7.84 (d, 2H),7.23-7.40 (m, 4H), 4.67 (m, 1H), 7.34 (m, 3H), 4.75 (br m, 1H), 4.05 (m,2H), 3.75 (br m, 1H), 3.30 (br m, 1H), 2.80-3.00 (br m, 2H), 1.90 (br m,1H), 1.6-1.8 (br m, 3H). MS(EI): 380(M⁺+H).

EXAMPLE 3461-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(3-benzylamino-phenyl)-methanonedihydrochloride

A.[3-(4-[3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester

By proceeding in a similar manner to the method described in EXAMPLE105B, but using 3-(Boc-amino)benzoic acid in place of5-tert-butoxycarbonylamino-nicotinic acid, there was prepared{3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester as a white solid. ¹H NMR (300 MHz, CDCl₃):δ7.40-7.50 (m, 2H), 7.22-7.37 (m, 2H), 7.04-7.15 (m, 4H), 4.75-4.90 (brm, 1H), 4.76 (s, 2H), 3.80-3.96 (br m, 1H), 3.00-3.25 (br m, 1H),2.68-2.95 (m, 2H), 1.40-2.05 (m partially obscured, 4H), 1.52 (s, 9H),1.45 (s, 18H). MS (CI): m/z 610 (M+H).

B.Benzyl-[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using benzyl bromide in place of 4-bromo-2-fluorobenzylbromide and using[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester, there was preparedbenzyl-[3-(4-[3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester as a white solid. ¹H NMR (300 MHz, CDCl₃):δ7.03-7.34 (m, 13H), 4.75-4.90 (m partially obscured, 1H), 4.84 (br s,2H), 4.77 (s, 2H), 3.69-3.85 (br m, 1H), 2.90-3.10 (br m, 1H), 2.65-2.90(m, 2H), 1.40-2.00 (m partially obscured, 4H), 1.45 (s, 18H), 1.41 (s,9H). MS (CI): m/z 700 (M+H).

C.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(3-benzylamino-phenyl)-methanonedihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but using preparedbenzyl-[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester, there was prepared1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-(3-benzylamino-phenyl)-methanonedihydrochloride as a white solid. ¹H NMR [300 MHz, (CD₃)₂SO]: δ8.26 (brs, 3H), 7.20-7.55 (m, 9H), 7.11 (tr, 1H), 6.66 (d, 1H), 6.57 (m, 2H),4.40-4.70 (br m, 1H), 4.30 (s, 2H), 4.15 (m, 1H), 4.01 (q, 2H),2.90-3.15 (br m, 1H), 2.65-2.90 (br m, 2H), 1.35-1.95 (br m, 4H). MS(ESI): m/z 400 (M+H).

EXAMPLE 3471-{4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[(naphthalen-2-ylmethyl)-amino]-phenyl}-methanonedihydrochloride

A.[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-naphthalen-2-ylmethyl-carbamicacid tert-butyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using 2-(bromomethyl)naphthalene in place of4-bromo-2-fluorobenzyl bromide and using[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester, there was prepared[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-naphthalen-2-ylmethyl-carbamicacid tert-butyl ester as a white solid. ¹H NMR (300 MHz, CDCl₃):δ7.61-7.80 (m, 4H), 7.38-7.45 (m, 3H), 6.99-7.34 (m, 8H), 5.00 (br s,2H), 4.70-4.90 (m partially obscured, 1H), 4.76 (s, 2H), 3.55-3.75 (brm, 1H), 2.70-2.95 (br m, 2H), 2.55-2.70 (m, 1H), 1.40-1.95 (m partiallyobscured, 4H), 1.45 (s, 18H), 1.42 (s, 9H). MS (ESI): m/z 650 (M+H).

B.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[(naphthalen-2-ylmethyl)-amino]-phenyl}-methanonedihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but using[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-naphthalen-2-ylmethyl-carbamicacid tert-butyl ester, there was prepared1-{4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[(naphthalen-2-ylmethyl)-amino]-phenyl}-methanonedihydrochloride as a white solid. ¹H NMR [300 MHz, (CD₃)₂SO]: δ8.22 (brs, 3H), 7.81-7.88 (m, 4H), 7.11-7.54 (m, 8H), 6.69 (d, 1H), 6.59 (s,1H), 6.54 (d, 1H), 4.45-4.65 (m partially obscured, 1H), 4.47 (s, 2H),4.01 (q, 2H), 3.60-3.80 (m partially obscured, 1H), 2.85-3.05 (br m,1H), 2.65-2.85 (br m, 2H), 1.30-1.95 (br m, 4H). MS (ESI): m/z 450(M+H).

EXAMPLE 3483-[(3-{1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-phenylamino)-methyl]-benzonitriledihydrochloride

A.[3-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-(3-cyano-benzyl)-carbamicacid tert-butyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using α-bromo-m-tolunitrile in place of 4-bromo-2-fluorobenzylbromide and using[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester, there was prepared[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-(3-cyano-benzyl)-carbamicacid tert-butyl ester as a white solid. ¹H NMR (300 MHz, CDCl₃):δ7.06-7.55 (m, 12H), 4.70-4.90 (m partially obscured, 1H), 4.86 (s, 2H),4.77 (s, 2H), 3.70-3.90 (br m, 1H), 2.95-3.20 (br m, 1H), 2.65-2.95 (brm, 2H), 1.40-2.00 (m partially obscured, 4H), 1.45 (s, 18H), 1.41 (s,9H). MS (CI): m/z 725 (M+H).

B.3-[(3-{1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-phenylamino)-methyl]-benzonitriledihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-(3-cyano-benzyl)-carbamicacid tert-butyl ester, there was prepared3-[(3-{1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-phenylamino)-methyl]-benzonitriledihydrochloride as a white solid. ¹H NMR [300 MHz, (CD₃)₂SO]: δ8.18 (brs, 3H), 7.75 (s, 1H), 7.65 (m, 2H), 7.49 (tr, 1H), 7.21-7.35 (m, 4H),7.08 (tr, 1H), 6.61 (d, 1H), 6.52 (m, 2H), 4.40-4.70 (br m, 1H), 4.33(s, 2H), 3.98 (q, 2H), 3.50-3.70 (m partially obscured, 1H), 2.85-3.10(br m, 1H), 2.65-2.85 (br m, 2H), 1.30-1.90 (br m, 4H). MS (ESI): m/z425 (M+H).

EXAMPLE 3491-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(4-bromo-benzylamino)-phenyl]-methanonedihydrochloride

A.(4-Bromo-benzyl)-[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester

By proceeding in a similar manner to the method described in EXAMPLE105C, but using 4-bromobenzyl bromide in place of 4-bromo-2-fluorobenzylbromide and using[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester, there was prepared(4-bromo-benzyl)-[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester as a clear oil. ¹H NMR (300 MHz, CDCl₃): δ7.41 (d,2H), 7.06-7.38 (m, 8H), 7.10 (d, 2H), 4.70-4.90 (br m, partiallyobscured, 1H), 4.78 (s, 2H), 4.77 (s, 2H), 4.25-4.45 (br m, 1H),3.70-3.85 (br m, 1H), 2.90-3.15 (br m, 1H), 2.65-2.90 (br m, 2H),1.40-2.00 (m partially obscured, 4H), 1.45 (s, 18H), 1.41 (s, 9H). MS(CI): m/z 778 (M+H).

B.1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(4-bromo-benzylamino)-phenyl]-methanonedihydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but using(4-bromo-benzyl)-[3-(4-{3-[N,N-bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidine-1-carbonyl)-phenyl]-carbamicacid tert-butyl ester, there was prepared1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(4-bromo-benzylamino)-phenyl]-methanonedihydrochloride as a white solid. ¹H NMR [300 MHz, (CD₃)₂SO]: δ8.28 (brs, 3H), 7.25-7.66 (m, 8H), 7.11 (tr, 1H), 6.64 (d, 1H), 6.55 (m, 2H),4.45-4.70 (br m, 1H), 4.28 (s, 2H), 4.15 (m, 1H), 4.01 (q, 2H),2.90-3.15 (br m, 1H), 2.65-2.90 (br m, 2H), 1.30-1.95 (br m, 4H). MS(ESI): m/z 480 (M+H).

EXAMPLE 350[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-[1,1′;4′,1″]terphenyl-3-yl-methanonehydrochloride

A.{4-[3-N,N-Di-(tert-butoxycarbonyl)aminomethyl)-phenyl]-piperidin-1-yl}-(3-bromo-phenyl)-methanone

By proceeding in a similar manner to the method described in EXAMPLE105B, but using 3-bromobenzoic acid in place of5-tert-butoxycarbonylamino-nicotinic acid, there was prepared{4-[3-N,N-di-(tert-butoxycarbonyl)aminomethyl)-phenyl]-piperidin-1-yl}-(3-bromo-phenyl)-methanoneas a colorless oil. ¹H NMR (300 MHz, CDCl₃): δ7.55 (m, 2H), 7.24-7.37(m, 2H), 7.08-7.16 (m, 4H), 4.75-4.92 (br m, 1H), 4.77 (s, 2H),3.75-3.90 (br m, 1H), 3.00-3.25 (br m, 1H), 2.70-3.00 (br m, 2H),1.50-2.00 (m partially obscured, 4H) 1.45 (s, 18H). MS (CI): m/z 573(M+H).

B.{4-[3-N,N-Di-(tert-butoxycarbonyl)aminomethyl)-phenyl]-piperidin-1-yl}-[1,1′;4′,1″]terphenyl-3-yl-methanone

By proceeding in a similar manner to the method described in EXAMPLE17D, but using 4-biphenylboronic acid in place of1-(5-phenylethyl-pyridine-3-carbonyl)-4-(pinacolatoboronyl)-1,2,3,6-tetrahydro-pyridineand{4-[3-N,N-di-(tert-butoxycarbonyl)aminomethyl)-phenyl]-piperidin-1-yl}-(3-bromo-phenyl)-methanonein place of N-(tert-butoxycarbonyl)-3-bromo-4-fluoro-benzylamine, therewas prepared{4-[3-N,N-di-(tert-butoxycarbonyl)aminomethyl)-phenyl]-piperidin-1-yl}-[1,1′;4′,1″]terphenyl-3-yl-methanoneas a yellow oil. ¹H NMR (300 MHz, CDCl₃): δ7.61-7.71 (m, 8H), 7.34-7.53(m, 6H), 7.14 (m, 3H), 4.80-5.00 (m, 1H), 4.77 (s, 2H), 3.85-4.05 (br m,1H), 3.00-3.25 (br m, 1H), 2.70-3.00 (br m, 2H), 1.50-2.05 (m, 4H), 1.44(s, 18H). MS (CI): m/z 647 (M+H).

C.[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-[1,1′;4′,1″]terphenyl-3-yl-methanonehydrochloride

By proceeding in a similar manner to the method described in EXAMPLE105D, but using{4-[3-N,N-di-(tert-butoxycarbonyl)aminomethyl)-phenyl]-piperidin-1-yl}-[1,1′;4′,1″]terphenyl-3-yl-methanone,there was prepared[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-[1,1′;4′,1″]terphenyl-3-yl-methanonehydrochloride as a cream-colored solid. ¹H NMR [300 MHz, (CD₃)₂SO]:δ8.24 (br s, 3H), 7.73-7.84 (m, 8H), 7.29-7.61 (m, 9H), 4.55-4.80 (br m,1H), 4.01 (q, 2H), 3.65-3.85 (br m, 1H), 2.75-3.05 (br m, 2H), 1.50-2.00(br m, 4H). MS (CI): m/z 447 (M+H).

EXAMPLE 351 4-(3-aminomethyl-phenyl)-piperidine-1-carboxylic acid(3,4-dichloro-phenyl)-amide trifluoroacetate

3,4-Dichlorophenyl isocyanate (60 mg, 0.319 mmol) was added to astirring solution of4-[3-(N,N-di-tert-butoxycarbonylaminomethyl)phenyl]piperidine (100 mg,0.256 mmol) in DCM (5 mL) at room temperature. After 16 hours thereaction was quenched with water (5 mL) and separated, and extracted theaqueous phase with DCM (5 mL). The combined organics were dried overanhydrous sodium sulfate, and concentrated to dryness. The residue waspurified by dry flash column chromatography on silica with 50:50,dichloromethane:ethyl acetate.4-[3-(N,N-di-tert-butoxycarbonylaminomethyl)phenyl]-piperidine-1-carboxylicacid (3,4-dichloro-phenyl)-amide was isolated as a colorless oil, whichwas dissolved in dichloromethane (25 mL), cooled at 0° C., and treatedwith trifluoroacetic acid (3 mL). The reaction mixture was stirred atroom temperature under nitrogen for 2 hours, and concentrated to drynessin vacuo. The residue was dissolved in 20% acetonitrile/water[containing 0.1% trifluoroacetic acid] (9 mL) and purified bypreparative reverse-phase HPLC (C-18, 10 micron reverse-phase column),eluting with 10% to 100% acetonitrile/water (containing 0.1%trifluoroacetic acid). The product fractions were combined and theacetonitrile removed in vacuo. The aqueous residue was frozen andlyophilized to give the title compound as an amorphous white solid (68mg, 53%). ¹H NMR [(CD₃)₂SO]: δ8.82 (s, H, NH); 7.88 (s, H); 7.84 (br s,3H, NH₃ ⁺); 7.46 (s, H); 7.37-7.22 (m, 5H); 4.24 (br d, 2H); 3.99 (s,2H); 2.89 (br t, 2H); 2.83-2.70 (m, H); 1.82-1.71 (m, 2H); 1.60-1.44 (m,2H). MS(Ion spray): 378 and 380 (M⁺+1).

EXAMPLE 352 4-(3-aminomethyl-phenyl)-piperidine-1-carboxylic acid2,3-dimethoxybenzylamide-trifluoroacetate

(3-Piperidin-4-yl-benzyl) carbamate Wang resin (EXAMPLE 122D) (60 μmol)was suspended in dichloromethane (2 mL) and added diisopropylethylamine(0.66 mmol) followed by phosgene (0.6 mmol of a 20% solution intoluene). The reaction mixture was shaken for 5 minutes before washingthe resin with toluene (×8). The resin was suspended in DMF (2 mL) andto this was added a solution of 2,3-dimethoxybenzylamine (0.6 mmol) inDMF (1.5 mL) and the reaction mixture shaken for 5 minutes beforewashing the resin with DMF (×3). The resin was then suspended indichloromethane (2 mL) and treated with TFA (0.5 mL). The reactionmixture was shaken for 5 minutes, before the resin was filtered off andthe filtrate concentrated to dryness to give the title compound (48μmol) as a pale yellow solid. MS (EI) 383 (M⁺).

By proceeding in a similar manner to the method described in EXAMPLES351 AND 352, the following compounds set forth in Table 7 were prepared,as the trifluoroacetate salts: TABLE 7 EG Structure M/Z MS area % 353

391 >95% 354

360 >95% 355

430 >95% 356

406 >95% 357

383 >95% 358

436 >95% 359

405 >95% 360

419 >95% 361

435 >95% 362

423 >95% 363

384 >95% 364

380 >95% 365

337 >95%In Vitro Test Procedure

Since all the actions of tryptase, as described in the backgroundsection, are dependent on its catalytic activity, then compounds thatinhibit its catalytic activity will potentially inhibit the actions oftryptase. Inhibition of this catalytic activity may be measured by thein vitro enzyme assay and the cellular assay.

Tryptase inhibition activity is confirmed using either isolated humanlung tryptase or recombinant human β tryptase expressed in yeast cells.Essentially equivalent results are obtained using isolated native enzymeor the expressed enzyme. The assay procedure employs a 96 wellmicroplate (Costar 3590) usingL-pyroglutamyl-L-prolyl-L-arginine-para-nitroanilide (S2366: Quadratech)as substrate (essentially as described by McEuen et. al. Biochem Pharm,1996, 52, pages 331-340). Assays are performed at room temperature using0.5 mM substrate (2×K_(m)) and the microplate is read on a microplatereader (Beckman Biomek Plate reader) at 405 nm wavelength. Theinhibition constant (Ki) for particular compounds of the presentinvention is set forth in Table 8. It was determined using the procedureset forth herein.

Materials and Methods for Tryptase primary screen (Chromogenic assay)

Assay Buffer

50 mM Tris (pH 8.2), 100 mM NaCl, 0.05% Tween 20, 50 ug/ml heparin.

Substrate

S2366 (Stock solutions of 2.5 mM).

Enzyme

Purified recombinant beta Tryptase Stocks of 310 ug/ml.

Protocol (Single Point Determination)

-   -   Add 60 ul of diluted substrate (final concentration of 500 uM in        assay buffer) to each well    -   Add compound in duplicates , final concentration of 20 uM,        volume 20 ul    -   Add enzyme at a final concentration of 50 ng/ml in a volume of        20 ul    -   Total volume for each well is 100 ul    -   Agitate briefly to mix and incubate at room temp in the dark for        30 minutes    -   Read absorbencies at 405 nM

Each plate has the following controls

Totals: 60 ul of substrate, 20 ul of buffer (with 0.2% finalconcentration of DMSO), 20 ul of enzyme

Non-specific: 60 ul of substrate, 40 ul of buffer (with 0.2% DMSO)

Totals: 60 ul of substrate, 20 ul of buffer (No DMSO), 20 ul of enzyme

Non-specific: 60 ul of substrate, 40 ul of buffer (No DMSO)

Protocol (IC₅₀ and Ki determination)

The protocol is essentially the same as above except that the compoundis added in duplicates at the following final concentrations: 0.01,0.03, 0.1, 0.3, 1, 3, 10 uM (All dilutions carried out manually). Forevery assay, whether single point or IC₅₀ determination, a standardcompound is used to derive IC₅₀ for comparison. From the IC 50 value,the Ki can be calculated using the following formula:Ki=IC₅₀/(1+[Substrate]/Km).

Using this procedure, Ki values with respect to tryptase for particularcompounds of the present invention are set forth in Table 8 below: TABLE8 EXAMPLE # NAME Tryptase Ki (nM) 13[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(5-phenethyl- 50thiophen-2-yl)-methanone hydrochloride 15[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(3- 1,070phenoxymethyl-phenyl)-methanone hydrochloride) 18[4-(5-Aminomethyl-2-methyl-phenyl)-piperidin-1-yl]-(5- 69phenethyl-pyridin-3-yl)-methanone di-hydrochloride) 194-(3-Aminomethyl-phenyl)-piperidin-1-yl]-[3-(5-phenyl- 1801,3,4-oxadiazol-2-yl)-phenyl]-methanone hydrochloride) 354-(3-Aminomethyl-phenyl)-1-(5-phenethyl-pyridine-3- 93carbonyl)-piperidine-4-carbonitrile 36[4-(3-Aminomethylphenyl)piperidin-1-yl]-(3,4-dichloro- 31phenyl)-methanone trifluoroacetate 481-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(4-chloro- 390phenyl)-methanone trifluoroacetate 491-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[5-(2- 390chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-phenyl}-methanone trifluoroacetate70 1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(4,5,6,7- 290tetrahydro-benzo[c]thiophen-1-yl)-methanone- trifluoroacetate. 831-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(4-fluoro- 870phenylethynyl)-phenyl]-methanone trifluoroacetate 921-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(5-chloro- 190thieno[3,2-b]thiophen-2-yl)-methanone trifluoroacetate 97[4-(3-Aminomethylphenyl)-piperidin-1-yl]-(4-phenylethyl- 450phenyl)-methanone hydrochloride 98[4-(3-Aminomethylphenyl)-piperidin-1-yl]-{3-[2-(2- 180hydroxyphenyl)-ethyl]-phenyl)-methanone hydrochloride 100[4-(5-Aminomethyl-thiophen-2-yl)-piperidin-1-yl]-(5- 490phenylethyl-pyridin-3-yl)-methanone di-hydrochloride 13[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(5- 50phenethyl-thiophen-2-yl)-methanone hydrochloride 15[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-(3- 1,070phenoxymethyl-phenyl)-methanone hydrochloride) 18[4-(5-Aminomethyl-2-methyl-phenyl)-piperidin-1-yl]- 69(5-phenethyl-pyridin-3-yl)-methanone di-hydrochloride) 354-(3-Aminomethyl-phenyl)-1-(5-phenethyl-pyridine-3- 93carbonyl)-piperidine-4-carbonitrile 481-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(4- 390chloro-phenyl)-methanone trifluoroacetate 491-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[5- 390(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-phenyl}- methanonetrifluoroacetate 70 1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1- 290(4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-methanone- trifluoroacetate.83 1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(4-fluoro- 870phenylethynyl)-phenyl]-methanone trifluoroacetate 921-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(5- 190chloro-thieno[3,2-b]thiophen-2-yl)-methanone trifluoroacetate 97[4-(3-Aminomethylphenyl)-piperidin-1-yl]-(4- 450phenylethyl-phenyl)-methanone hydrochloride 98[4-(3-Aminomethylphenyl)-piperidin-1-yl]-{3-[2-(2- 180hydroxyphenyl)-ethyl]-phenyl)-methanone hydrochloride 100[4-(5-Aminomethyl-thiophen-2-yl)-piperidin-1-yl]-(5- 490phenylethyl-pyridin-3-yl)-methanone di-hydrochloride

This data clearly shows that compounds of the present invention exhibittryptase inhibition activity. Consequently, compounds of the presentinvention readily have applications in pharmaceutical compositions fortreating a wide variety of tryptase related conditions, and naturally,in methods for treating such conditions in patients.

The present invention is not to be limited in scope by the specificembodiments describe herein. Indeed, various modifications of theinvention in addition to those described herein will become apparent tothose skilled in the art from the foregoing description and theaccompanying figures. Such modifications are intended to fall within thescope of the appended claims.

Various publications are cited herein, the disclosures of which areincorporated by reference in their entireties.

1. A compound of formula (I):

such that Ar is an aryl group or a heteroaryl group, and the

group is beta to the

group on the aryl, wherein:

is a single or a double bond; R¹ and R² are each independently hydrogenor lower alkyl; R³ is aryl, arylalkenyl, cycloalkenyl, cycloalkyl,heteroaryl, heteroarylalkenyl, heterocycloalkenyl, a carbon linkedheterocycloalkyl or alkyl optionally substituted by one or more groupsselected from hydroxy, alkoxy, alkyloxycarbonylamino, cycloalkyl,heterocycloalkyl, R⁶, —OR⁶, —S(O)_(m)R⁶ or —C(═O)—R⁶; R⁴ is hydrogen,acyl, alkoxy, alkyloxycarbonyl, carboxy, cyano, halo, hydroxy,—C(═O)—NY¹Y² or alkyl optionally substituted with alkoxy,alkylcarbonylamino, alkylsulfonylamino, hydroxy, —S(O)M-alkyl or —NY¹Y²;R⁵ is hydrogen, acyl, alkoxy, alkyloxycarbonyl, aryl, carboxy, cyano,halo, heteroaryl, heteroaryloxy, heterocycloalkyl, heterocycloalkyloxy,heterocycloalkylalkyloxy, heteroarylalkyloxy, hydroxy, trifluoromethyl,—C(═O)—NY¹Y², —NY¹Y², —Z¹—C₂₋₆alkylene-R⁷ or alkyl optionallysubstituted with alkoxy, alkylcarbonylamino, alkylsulfonylamino, aryl,heteroaryl, heterocycloalkyl, hydroxy, ureido, —C(═O)—NY¹Y², —SO₂—NY¹Y²,—S(O)_(m)-alkyl or —NY¹Y²; R⁶ is aryl or heteroaryl; R⁷ is hydroxy,alkoxy, ureido, —C(═O)—NY¹Y², —SO2—NY1Y², —S(O)_(m)-alkyl or —NY¹Y²; R⁸is hydrogen or lower alkyl; Y¹ and Y² are independently hydrogen,alkenyl, alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heteroarylalkylor heterocycloalkyl; or the group —NY¹Y² may form a cyclic amine; Z¹ isO, S(O)_(m) or NR⁸; m is zero or an integer 1 to 2; n is zero or aninteger 1 to 4; an N-oxide of said compound, a prodrug of said compound,a pharmaceutically acceptable salt of said compound, a solvate of saidcompound, and a hydrate of said compound.
 2. The compound of claim 1,wherein R¹ and/or R² is hydrogen, and R³ is an aryl or an heteroaryl. 3.The compound of claim 2, wherein said R³ aryl comprises a phenyl or anaphthyl.
 4. The compound of claim 2, wherein said R³ aryl issubstituted with at least one substituent.
 5. The compound of claim 4,wherein said substituent is selected from the group consisting of a haloatom, an alkyl substituted by aryl, an alkyl substituted by aryloxy, analkyl substituted by aroyl, an alkyl substituted by heteroaryl, anarylalkynyl, a heteroarylalkynyl, an aryl, a heteroaryl, an arylalkenyland an arylalkyloxy.
 6. The compound of claim 5, wherein said aryl orheteroaryl of said substituent is further substituted by at least onearyl group substituent.
 7. The compound of claim 2, wherein saidheteroaryl comprises a pyridyl, a quinolinyl, a thienyl, a furanyl, oran indolyl.
 8. The compound of claim 7, wherein said heteroaryl issubstituted with at least one substituent.
 9. The compound of claim 8,wherein said substituent comprises an alkyl, an alkyl substituted by anaryl, an alkyl substituted by an aryloxy, an alkyl substituted by anaroyl, an alkyl substituted heteroaryl, an arylalkynyl, aheteroarylalkynyl, a heteroaryl, an arylalkenyl or an arylalkyoxy. 10.The compound of claim 9, wherein said aryl of said substituent isfurther substituted by at least one aryl substituent.
 11. The compoundof claim 1, wherein R⁴ comprises hydrogen or a cyano group.
 12. Thecompound of claim 1, wherein R⁵ comprises a hydrogen, a lower alkyl, ora halo.
 13. The compound of claim 1, wherein

is a single bond.
 14. The compound of claim 1, wherein n=2.
 15. Thecompound of claim 1, wherein: Ar comprises a phenyl group;R¹=R²=hydrogen; R³ comprises an aryl, a naphthyl, or a heteroaryl; R⁴comprises hydrogen or a cyano group; R⁵ comprises hydrogen, a loweralkyl, or a halo;

represents a single bond; and n=2.
 16. The compound of claim 15, whereinsaid aryl or said naphthyl of R³ is substituted with at least onesubstituent comprising a halo atom, an alkyl substituted by aryl, analkyl substituted by aryloxy, an alkyl substituted by aroyl, an alkylsubstituted by aryloxy, an alkyl substituted by aroyl, an alkylsubstituted by a heteroaryl, an arylalkynyl, a heteroarylalkynyl, anaryl, a heteroaryl, an arylalkenyl, or an arylalkyloxy.
 17. The compoundof claim 16, wherein said aryl or said heteroaryl of said substituent isfurther substituted by at least one aryl substituent.
 18. The compoundof claim 15, wherein said heteroaryl of R³ is substituted by at leastone substituent comprising a pyridyl, a quinolinyl, a thienyl a furanyl,or an indolyl.
 19. The compound of claim 18, wherein said substituent ofsaid heteroaryl is further substituted by at least one moiety comprisingan alkyl substituted by an aryl, an alkyl substituted by an aryloxy, analkyl substituted by an aroyl, an alkyl substituted heteroaryl, anarylalkynyl, a heteroarylalkynyl, a heteroaryl, an arylalkenyl, or anarylalkyloxy.
 20. The compound of claim 19, wherein an aryl of saidmoiety is further substituted by at least one aryl substituent.
 21. Acompound of formula (Ia):

wherein R³ is aryl, arylalkenyl, cycloalkenyl, cycloalkyl, heteroaryl,heteroarylalkenyl, heterocycloalkenyl, a carbon linked heterocycloalkylor alkyl optionally substituted by one or more groups selected fromhydroxy, alkoxy, alkyloxycarbonylamino, cycloalkyl, heterocycloalkyl,R⁶, —OR⁶, —S(O)_(m)R⁶ or —C(═O)—R⁶; R⁴ is hydrogen, acyl, alkoxy,alkyloxycarbonyl, carboxy, cyano, halo, hydroxy, —C(═O)—NY¹Y² or alkyloptionally substituted with alkoxy, alkylcarbonylamino,alkylsulfonylamino, hydroxy, —S(O)_(m)-alkyl or —NY¹Y²; and R⁵ ishydrogen, acyl, alkoxy, alkyloxycarbonyl, aryl, carboxy, cyano, halo,heteroaryl, heteroaryloxy, heterocycloalkyl, heterocycloalkyloxy,heterocycloalkylalkyloxy, heteroarylalkyloxy, hydroxy, trifluoromethyl,—C(═O)—NY¹Y², —NY¹Y², —Z¹—C₂₋₆alkylene-R⁷ or alkyl optionallysubstituted with alkoxy, alkylcarbonylamino, alkylsulfonylamino, aryl,heteroaryl, heterocycloalkyl, hydroxy, ureido, —C(═O)—NY¹Y², —SO₂—NY¹Y²,—S(O)_(m)-alkyl or —NY¹Y², and, a corresponding N-oxide of saidcompound, a prodrug of said compound, a pharmaceutically acceptable saltof said compound, a solvate of said compound, an N-oxides and prodrugs.22. The compound of claim 21, wherein R³ is an aryl comprising a phenylor a naphthyl.
 23. The compound of claim 22, wherein said aryl issubstituted by at least one substituent comprising a halo atom, an alkylsubstituted by an aryl, an alkyl substituted by a heteroaryl.
 24. Thecompound of claim 23, wherein said aryl or heteroaryl of saidsubstituent is further substituted by at least one aryl groupsubstituent.
 25. The compound of claim 21, wherein R³ comprisesphenylC₁₋₃alkylpyridyl [e.g. 5-phenylethyl-pyrid-3-yl],phenylC₁₋₃alkylthienyl [e.g. 5-phenylethyl-thien-2-yl] or indolyl [e.g.indol-6-yl].
 26. The compound of claim 21, wherein R³ is a heteroarylcomprising a pyridyl, a quinolinyl, a thienyl, a furanyl, or an indolyl.27. The compound of claim 26, wherein said heteroaryl is substituted byat least one substituent comprising an alkyl substituted by an aryl, oran alkyl substituted by a heteroaryl.
 28. The compound of claim 27,wherein said aryl and said heteroaryl of said substituent are furthersubstituted by at least one aryl group substituent.
 29. The compound ofclaim 28, wherein R³ comprises phenylC₁₋₃alkylpyridyl [e.g.5-phenylethyl-pyrid-3-yl], phenylC₁₋₃alkylthienyl [e.g.5-phenylethyl-thien-2-yl], or indolyl [e.g. indol-6-yl].
 30. Thecompound of claim 21, wherein R⁴ comprises a hydrogen or a cyano. 31.The compound of claim 21, wherein R⁵ comprises a hydrogen, a lower alkylor a halo.
 32. The compound of claim 31, wherein R⁵ comprises a methylor a fluoro.
 33. The compound of claim 31, wherein R⁵ is attached to thephenyl ring of formula (Ia) in the position para to the CH₂NH₂ group.34. The compound of claim 21, wherein: R³ is a phenyl, a naphthyl, aheteroaryl selected from the group consisting a pyridyl, a quinolinyl, athienyl, a furanyl, and an indolyl, a phenyl substituted by at least onesubstituent, a naphthyl substituted by at least one substituent, or aheteroaryl selected from the group consisting a pyridyl, a quinolinyl, athienyl, a furanyl, and an indolyl, that is substituted by at least onesubstituent, wherein said substituent is selected from the groupconsisting of a halo atom, an alkyl substituted by aryl, and alkylsubstituted heteroaryl, wherein the aryl or heteroaryl groups arefurther substituted by one or more aryl group substituents; R⁴ compriseshydrogen or a cyano; and R⁵ comprises hydrogen, a lower alkyl or a halo.35. The compound of claim 34, wherein: R³ comprisesphenylC₁₋₃alkylpyridyl [e.g. 5-phenylethyl-pyrid-3-yl],phenylC₁₋₃alkylthienyl [e.g. 5-phenylethyl-thien-2-yl] or indolyl [e.g.indol-6-yl; R⁴ comprises a hydrogen or a cyano; and R⁵ comprises amethyl or a fluoro, and is attached to the phenyl ring of formula (Ib)in the position para to the CH₂NH₂ group.
 36. A compound of formula(Ib):

wherein R³ is aryl, arylalkenyl, cycloalkenyl, cycloalkyl, heteroaryl,heteroarylalkenyl, heterocycloalkenyl, a carbon linked heterocycloalkylor alkyl optionally substituted by one or more groups selected fromhydroxy, alkoxy, alkyloxycarbonylamino, cycloalkyl, heterocycloalkyl,R⁶, —OR⁶, —S(O)_(m)R⁶ or —C(═O)—R⁶; R⁴ is hydrogen, acyl, alkoxy,alkyloxycarbonyl, carboxy, cyano, halo, hydroxy, —C(═O)—NY¹Y² or alkyloptionally substituted with alkoxy, alkylcarbonylamino,alkylsulfonylamino, hydroxy, —S(O)_(m)-alkyl or —NY¹Y²; and R⁵ ishydrogen, acyl, alkoxy, alkyloxycarbonyl, aryl, carboxy, cyano, halo,heteroaryl, heteroaryloxy, heterocycloalkyl, heterocycloalkyloxy,heterocycloalkylalkyloxy, heteroarylalkyloxy, hydroxy, trifluoromethyl,—C(═O)—NY¹Y², —NY¹Y², —Z¹-C₂₋₆alkylene-R⁷ or alkyl optionallysubstituted with alkoxy, alkylcarbonylamino, alkylsulfonylamino, aryl,heteroaryl, heterocycloalkyl, hydroxy, ureido, —C(═O)—NY¹Y², —SO₂—NY¹Y²,—S(O)_(m)-alkyl or —NY¹Y², and, a corresponding N-oxide of saidcompound, a prodrug of said compound, a pharmaceutically acceptable saltof said compound, a solvate of said compound, an N-oxides and prodrugs.37. The compound of claim 36, wherein R³ is an aryl comprising a phenylor a naphthyl.
 38. The compound of claim 37, wherein said aryl issubstituted by at least one substituent comprising a halo atom, an alkylsubstituted by an aryl, an alkyl substituted by a heteroaryl.
 39. Thecompound of claim 38, wherein said aryl or heteroaryl of saidsubstituent is further substituted by at least one aryl groupsubstituent.
 40. The compound of claim 36, wherein R³ is a heteroarylcomprising a pyridyl, a quinolinyl, a thienyl, a furanyl, or an indolyl.41. The compound of claim 41, wherein said heteroaryl is substituted byat least one substituent comprising an alkyl substituted by an aryl, oran alkyl substituted by a heteroaryl.
 42. The compound of claim 42,wherein said aryl and said heteroaryl of said substituent are furthersubstituted by at least one aryl group substituent.
 43. The compound ofclaim 36, wherein R³ comprises phenylC₁₋₃alkylpyridyl [e.g.5-phenylethyl-pyrid-3-yl], phenyl]C₁₋₃alkylthienyl [e.g.5-phenylethyl-thien-2-yl], or indolyl [e.g. indol-6-yl].
 44. Thecompound of claim 36, wherein R⁴ comprises a hydrogen or a cyano. 45.The compound of claim 36, wherein R⁵ comprises a hydrogen, a lower alkylor a halo.
 46. The compound of claim 45, wherein R⁵ comprises a methylor a fluoro.
 47. The compound of claim 45, wherein R⁵ is attached to thephenyl ring of formula (Ib) in the position para to the CH₂NH₂ group.48. The compound of claim 36, wherein: R³ is a phenyl, a naphthyl, aheteroaryl selected from the group consisting a pyridyl, a quinolinyl, athienyl, a furanyl, and an indolyl, a phenyl substituted by at least onesubstituent, a naphthyl substituted by at least one substituent, or aheteroaryl selected from the group consisting a pyridyl, a quinolinyl, athienyl, a furanyl, and an indolyl, that is substituted by at least onesubstituent, wherein said substituent is selected from the groupconsisting of a halo atom, an alkyl substituted by aryl, and alkylsubstituted heteroaryl, wherein the aryl or heteroaryl groups arefurther substituted by one or more aryl group substituents; R⁴ compriseshydrogen or a cyano; and R⁵ comprises hydrogen, a lower alkyl or a halo.49. The compound of claim 48, wherein: R³ comprisesphenylC₁₋₃alkylpyridyl [e.g. 5-phenylethyl-pyrid-3-yl],phenylC₁₋₃alkylthienyl [e.g. 5-phenylethyl-thien-2-yl] or indolyl [e.g.indol-6-yl; R⁴ comprises a hydrogen or a cyano; and R⁵ comprises amethyl or a fluoro, and is attached to the phenyl ring of formula (Ib)in the position para to the CH₂NH₂ group.
 50. The compound of claim 1,selected from the group consisting of:3-[1-(5-phenylethynyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamine;3-[1-(3-phenylethyl-benzoyl)-piperidin-4-yl]-benzylamine;3-{1-[3-(4-hydroxyphenyl)ethyl-benzoyl]-piperidin-4-yl}-benzylamine;3-{1-[3-(6-amino-pyridin-3-yl)ethyl-benzoyl]-piperidin-4-yl}-benzylamine;3-[1-(5-phenylethyl-thiophene-2-carbonyl)-piperidin-4-yl]-benzylamine;4-fluoro-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamine;4-methyl-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamine;3-[1-(indole-6-carbonyl)-piperidin-4-yl]-benzylamine;4-(3-aminomethyl-phenyl)-1-(5-phenethyl-pyridine-3-carbonyl)-piperidine-4-carbonitrile[4-(3-aminomethylphenyl)piperidin-1-yl]-(3,4-dichlorophenyl)methanone;1-{1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-3-methylsulfanyl-6,7-dihydro-5H-benzo[c]thiophen-4-onetrifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(3-methylsulfanyl-6,7-dihydro-benzo[c]thiophen-1-yl)-methanonetrifluoroacetate;1-{1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-3-ethylsulfanyl-6,6-dimethyl-6,7-dihydro-5H-benzo[c]thiophen-4-onetrifluoroacetate;1-{1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-3-propylsulfanyl-6,7-dihydro-5H-benzo[c]thiophen-4-onetrifluoroacetate;1-{1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-3-isopropylsulfanyl-6,7-dihydro-5H-benzo[c]thiophen-4-onetrifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-benzo[b]thiophen-2-yl-methanone-trifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-4-hydroxy-piperidin-1-yl]-1-(5-phenethyl-pyridin-3-yl)-methanone-ditrifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(1-methyl-1H-indol-3-yl)-methanone-trifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(2-fluoro-phenylethynyl)-phenyl]-methanonetrifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[2-(2-fluoro-phenyl)-ethyl]-phenyl}-methanonetrifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[2-(6-amino-pyridin-3-yl)-ethyl]-phenyl}-methanonetri-trifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(6-chloro-thieno[3,2-b]thiophen-2-yl)-methanonetrifluoroacetate; (3R,4S) and (3S,4R)-4-(3-Aminomethyl-phenyl)-1-(5-phenethyl-pyridine-3-carbonyl)-piperidine-3-carboxylicacid ethyl ester dihydrochloride;3-[1-(5-Phenylethynyl-furan-2-carbonyl)-piperidin-4-yl]-benzylaminetrifluoroacetate; 4-(3-Aminomethyl-phenyl)-piperidine-1-carboxylic acid(3,4-dichloro-phenyl)-amide trifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(2,3-dihydro-benzofuran-5-yl)-methanone;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(5,6-dichloro-pyridin-3-yl)-methanone;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(3-bromo-4-fluoro-phenyl)-methanone;(E)-1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-3-(2-nitro-phenyl)-propenone;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(3-bromo-5-iodo-phenyl)-methanone;and (E)-1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-3-phenyl-propenone.51. A pharmaceutical composition comprising a compound of claim 1 and apharmaceutically acceptable carrier thereof.
 52. The pharmaceuticalcomposition of claim 51, wherein said compound is selected from thegroup consisting of:3-[1-(5-phenylethynyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamine;3-[1-(3-phenylethyl-benzoyl)-piperidin-4-yl]-benzylamine;3-(1-[3-(4-hydroxyphenyl)ethyl-benzoyl]-piperidin-4-yl)-benzylamine;3-{1-[3-(6-amino-pyridin-3-yl)ethyl-benzoyl]-piperidin-4-yl}-benzylamine;3-[1-(5-phenylethyl-thiophene-2-carbonyl)-piperidin-4-yl]-benzylamine;4-fluoro-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamine;4-methyl-3-[1-(5-phenylethyl-pyridine-3-carbonyl)-piperidin-4-yl]-benzylamine;3-[1-(indole-6-carbonyl)-piperidin-4-yl]-benzylamine;4-(3-aminomethyl-phenyl)-1-(5-phenethyl-pyridine-3-carbonyl)-piperidine-4-carbonitrile[4-(3-aminomethylphenyl)piperidin-1-yl]-(3,4-dichlorophenyl)methanone;1-{1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-3-methylsulfanyl-6,7-dihydro-5H-benzo[c]thiophen-4-onetrifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(3-methylsulfanyl-6,7-dihydro-benzo[c]thiophen-1-yl)-methanonetrifluoroacetate;1-{1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-3-ethylsulfanyl-6,6-dimethyl-6,7-dihydro-5H-benzo[c]thiophen-4-onetrifluoroacetate;1-{1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-3-propylsulfanyl-6,7-dihydro-5H-benzo[c]thiophen-4-onetrifluoroacetate;1-{1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-methanoyl}-3-isopropylsulfanyl-6,7-dihydro-5H-benzo[c]thiophen-4-onetrifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-benzo[b]thiophen-2-yl-methanone-trifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-4-hydroxy-piperidin-1-yl]-1-(5-phenethyl-pyridin-3-yl)-methanone-ditrifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(1-methyl-1H-indol-3-yl)-methanone-trifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-[3-(2-fluoro-phenylethynyl)-phenyl]-methanonetrifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[2-(2-fluoro-phenyl)-ethyl]-phenyl}-methanonetrifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-{3-[2-(6-amino-pyridin-3-yl)-ethyl]-phenyl}-methanonetri-trifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(6-chloro-thieno[3,2-b]thiophen-2-yl)-methanonetrifluoroacetate; (3R,4S) and (3S,4R)-4-(3-Aminomethyl-phenyl)-1-(5-phenethyl-pyridine-3-carbonyl)-piperidine-3-carboxylicacid ethyl ester dihydrochloride;3-[1-(5-Phenylethynyl-furan-2-carbonyl)-piperidin-4-yl]-benzylaminetrifluoroacetate; 4-(3-Aminomethyl-phenyl)-piperidine-1-carboxylic acid(3,4-dichloro-phenyl)-amide trifluoroacetate;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(2,3-dihydro-benzofuran-5-yl)-methanone;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(5,6-dichloro-pyridin-3-yl)-methanone;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(3-bromo-4-fluoro-phenyl)-methanone;(E)-1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-3-(2-nitro-phenyl)-propenone;1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-1-(3-bromo-5-iodo-phenyl)-methanone;(E)-1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-3-phenyl-propenone; and1-[4-(3-Aminomethyl-phenyl)-piperidin-1-yl]-3-cyclohexyl-propan-1-one.53. A pharmaceutical composition comprising a compound of claim 21 and apharmaceutically acceptable carrier thereof.
 54. A pharmaceuticalcomposition comprising a compound of claim 36 and a pharmaceuticallyacceptable carrier thereof.
 55. A method for treating a patientsuffering from, or subject to, a condition that can be ameliorated bythe administration of an inhibitor of tryptase, wherein the methodcomprises administering to the patient an effective amount of a compoundof claim
 1. 56. The method of claim 55, wherein the condition comprisesinflammatory disease, a disease of joint cartilage destruction, ocularconjunctivitis, vernal conjunctivitis, inflammatory bowel disease,asthma, allergic rhinitis, an interstitial lung disease, fibrosis,sceleroderma, pulmonary fibrosis, liver cirrhosis, myocardial fibrosis,a neurofibroma, a hypertrophic scar, a dermatological condition, acondition related to atherosclerotic plaque rupture, periodontaldisease, diabetic retinopathy, tumor growth, anaphylaxis, multiplesclerosis, a peptic ulcer, or a syncytial viral infection.
 57. Themethod of claim 56, wherein the inflammatory disease comprises jointinflammation, arthritis, rheumatoid arthritis, rheumatoid spondylitis,gouty arthritis, traumatic arthritis, rubella arthritis, psoriaticarthritis, or osteoarthritis; the dermatological condition comprisesatopic dermatitis or psoriasis; and the condition related toatherosclerotic plaque rupture comprises myocardial infarction, stroke,or angina.
 58. A method for treating a patient suffering from, orsubject to, a condition that can be ameliorated by the administration ofan inhibitor of tryptase, wherein the method comprises administering tothe patient an effective amount of a compound of claim
 21. 59. Themethod of claim 58, wherein the condition comprises inflammatorydisease, a disease of joint cartilage destruction, ocularconjunctivitis, vernal conjunctivitis, inflammatory bowel disease,asthma, allergic rhinitis, an interstitial lung disease, fibrosis,sceleroderma, pulmonary fibrosis, liver cirrhosis, myocardial fibrosis,a neurofibroma, a hypertrophic scar, a dermatological condition, acondition related to atherosclerotic plaque rupture, periodontaldisease, diabetic retinopathy, tumor growth, anaphylaxis, multiplesclerosis, a peptic ulcer, or a syncytial viral infection.
 60. Themethod of claim 59, wherein the inflammatory disease comprises jointinflammation, arthritis, rheumatoid arthritis, rheumatoid spondylitis,gouty arthritis, traumatic arthritis, rubella arthritis, psoriaticarthritis, or osteoarthritis; the dermatological condition comprisesatopic dermatitis or psoriasis; and the condition related toatherosclerotic plaque rupture comprises myocardial infarction, stroke,or angina.
 61. A method for treating a patient suffering from, orsubject to, a condition that can be ameliorated by the administration ofan inhibitor of tryptase, wherein the method comprises administering tothe patient an effective amount of a compound of claim
 36. 62. Themethod of claim 61, wherein the condition comprises inflammatorydisease, a disease of joint cartilage destruction, ocularconjunctivitis, vernal conjunctivitis, inflammatory bowel disease,asthma, allergic rhinitis, an interstitial lung disease, fibrosis,sceleroderma, pulmonary fibrosis, liver cirrhosis, myocardial fibrosis,a neurofibroma, a hypertrophic scar, a dermatological condition, acondition related to atherosclerotic plaque rupture, periodontaldisease, diabetic retinopathy, tumor growth, anaphylaxis, multiplesclerosis, a peptic ulcer, or a syncytial viral infection.
 63. Themethod of claim 62, wherein the inflammatory disease comprises jointinflammation, arthritis, rheumatoid arthritis, rheumatoid spondylitis,gouty arthritis, traumatic arthritis, rubella arthritis, psoriaticarthritis, or osteoarthritis; the dermatological condition comprisesatopic dermatitis or psoriasis; and the condition related toatherosclerotic plaque rupture comprises myocardial infarction, stroke,or angina.
 64. A pharmaceutical composition comprising a compound ofclaim 1 and a second compound selected from the group consisting of abeta andrenergic agonist, an anticholinergic, an anti-inflammatorycorticosteroid, and an anti-inflammatory agent; and a pharmaceuticallyacceptable carrier thereof.
 65. The pharmaceutical composition of claim64, wherein the beta andrenergic agonist comprises albuterol,terbutaline, formoterol, fenoterol or prenaline; the anticholinergiccomprises ipratropium bromide; the anti-inflammatory corticosteroidcomprises beclomethasone dipropionate, triamcinolone acetonide,flunisolide or dexamethasone; and the anti-inflammatory agent comprisessodium cromoglycate or nedocromil sodium.
 66. A pharmaceuticalcomposition comprising a compound of formula 21 and a second compoundselected from the group consisting of a beta andrenergic agonist, ananticholinergic, an anti-inflammatory corticosteroid, and ananti-inflammatory agent; and a pharmaceutically acceptable carrierthereof.
 67. The pharmaceutical composition of claim 66, wherein thebeta andrenergic agonist comprises albuterol, terbutaline, formoterol,fenoterol or prenaline; the anticholinergic comprises ipratropiumbromide; the anti-inflammatory corticosteroid comprises beclomethasonedipropionate, triamcinolone acetonide, flunisolide or dexamethasone; andthe anti-inflammatory agent comprises sodium cromoglycate or nedocromilsodium.
 68. A pharmaceutical composition comprising a compound claim 36and a second compound selected from the group consisting of a betaandrenergic agonist, an anticholinergic, an anti-inflammatorycorticosteroid, and an anti-inflammatory agent; and a pharmaceuticallyacceptable carrier thereof.
 69. The pharmaceutical composition of claim66, wherein the beta andrenergic agonist comprises albuterol,terbutaline, formoterol, fenoterol or prenaline; the anticholinergiccomprises ipratropium bromide; the anti-inflammatory corticosteroidcomprises beclomethasone dipropionate, triamcinolone acetonide,flunisolide or dexamethasone; and the anti-inflammatory agent comprisessodium cromoglycate or nedocromil sodium.
 70. A method for treating apatient suffering from asthma, comprising administering to the patient acombination of a compound of claim 1, and a second compound selectedfrom the group consisting of a beta andrenergic agonist, ananticholinergic, an anti-inflammatory corticosteroid, and ananti-inflammatory agent
 71. A method for treating a patient sufferingfrom asthma, comprising administering to the patient a combination of acompound of claim 21, and a second compound selected from the groupconsisting of a beta andrenergic agonist, an anticholinergic, ananti-inflammatory corticosteroid, and an anti-inflammatory agent.
 72. Amethod for treating a patient suffering from asthma, comprisingadministering to the patient a combination of a compound of claim 36,and a second compound selected from the group consisting of a betaandrenergic agonist, an anticholinergic, an anti-inflammatorycorticosteroid, and an anti-inflammatory agent.